TW201529555A - Anthracene derivative and method for synthesizing the same - Google Patents

Abstract

It is an object to provide a novel method for synthesizing an anthracene derivative with the small number of steps. It is another object to provide a novel anthracene derivative. It is further another object to provide a light-emitting element, a light-emitting device, and an electronic device, each using the anthracene derivative. A method for synthesizing an anthracene derivative represented by a general formula (1) is provided by coupling a 9-arylanthracene derivative having an active site at a 10-position with a 9-arylcarbazole derivative having an active site in an aryl group using metal, a metal compound, or a metal catalyst.

Description

Anthracene derivative and its preparation method

The present invention relates to a method for synthesizing an anthracene derivative. The invention also relates to an anthracene derivative. The invention further relates to a current-excited light-emitting element and a light-emitting device and an electronic device each having the same.

In recent years, research and development of light-emitting elements using electroluminescence have been widely conducted. A structure in which a substance having a light-emitting property is inserted between a pair of electrodes is used as a basic structure of the light-emitting elements. Luminescence from a substance having luminescent properties can be obtained by applying a voltage to the element.

Since the light-emitting element is a self-luminous element, there is an advantage that the visibility of the pixel is higher than that of the liquid crystal display and the backlight is not required. Therefore, the light-emitting element is considered to be suitable as a flat display element. In addition, the light-emitting element can be made thin and light, which is a big advantage. Moreover, the light-emitting element has a characteristic that the reaction speed is extremely fast.

Furthermore, since the light-emitting elements can be formed in the form of a film, planar light emission can be easily obtained by forming a large-area element. This feature is difficult to be represented by a point source represented by an incandescent lamp or LED, or by a fluorescent lamp. Line source is obtained. Therefore, the light-emitting element has high utility as a planar light source to which illumination or the like can be applied.

Light-emitting elements using electroluminescence are roughly classified according to whether or not they use an organic compound or an inorganic compound as a substance having luminescent properties.

In the case where the substance having the luminescent property is an organic compound, electrons and holes are caused to flow in a layer from a pair of electrodes to a layer containing an organic compound having luminescent properties by applying a voltage to the light-emitting element. Then, the organic compound having luminescent properties is excited by the recombination of the carriers (electrodes and holes), and emits light when the excited state returns to the ground state. Because of this mechanism, this type of light-emitting element is called a current-excited type of light-emitting element.

It should be noted that the excited state formed by the organic compound may be a singlet excited state or a triplet excited state. Luminescence from a singlet excited state is referred to as fluorescence, and illumination from a triplet excited state is referred to as phosphorescence.

In order to overcome many problems derived from the material of the light-emitting element and to improve the characteristics of the element, improvement of the element structure, material development, and the like are performed.

For example, an anthracene derivative has been developed as a material for a light-emitting element (see Document 1: Japanese Published Patent Application No. 2003-238534). However, in order to synthesize the anthracene derivative disclosed in Document 1, several steps are required. Therefore, the yield is not advantageous and requires a long synthesis period.

In view of the above problems, it is an object of the present invention to provide a novel method for synthesizing an anthracene derivative in a few steps. Another object is to provide a novel anthracene derivative. A still further object is to provide a light-emitting element, a light-emitting device, and an electronic device using an anthracene derivative, respectively.

One aspect of the present invention is a process for synthesizing an anthracene derivative represented by the formula (1) by reacting a 9-arylindole derivative having an active position at a 10-position with an aryl group The 9-arylcarbazole derivative having an active position thereon is coupled using a metal, a metal compound or a metal catalyst.

In the formula (1), each of R ¹ to R ⁸ represents hydrogen, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms; and Ar ¹ represents 6 to 25 carbon atoms. Aryl; Ar ² represents an extended aryl group having 6 to 25 carbon atoms; and each of A ¹ and A ² represents hydrogen, an aryl group having 6 to 25 carbon atoms or an alkane having 1 to 4 carbon atoms base.

Another aspect of the present invention is a process for synthesizing an anthracene derivative represented by the formula (1) by substituting an anthracene derivative represented by the formula (2) with a formula (3) The carbazole derivative is coupled using a metal, a metal compound or a metal catalyst.

In the general formulae (1) to (3), each of R ¹ to R ⁸ represents hydrogen, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms; and Ar ¹ represents having 6 to Aryl group of 25 carbon atoms; Ar ² represents an extended aryl group having 6 to 25 carbon atoms; each of A ¹ and A ² represents hydrogen, an aryl group having 6 to 25 carbon atoms or has 1 to 4 carbons The alkyl group of the atom; and each of X ³ and X ⁶ represents an active site.

In the above synthesis, copper, iron or the like can be provided as the metal. Copper iodide or the like can be provided as the metal compound. A palladium catalyst, a nickel catalyst or the like can be provided as a metal catalyst.

In the above synthesis, boric acid or organoboron is preferably coupled to the halogen at the active site. In other words, it is preferred that one of the active sites is boric acid or organic boron, and the others are halogen. When boric acid or organoboron is coupled to the halogen at the active site, a high yield of anthracene derivatives can be obtained, which is one of the objects of the present invention.

Another aspect of the present invention is a process for synthesizing an anthracene derivative represented by the formula (1) by subjecting a 9-aryl-10-hydrazine halide to (carbazol-9-yl) The aryl boronic acid is coupled using a metal catalyst.

In the formula (1), each of R ¹ to R ⁸ represents hydrogen, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms; and Ar ¹ represents 6 to 25 carbon atoms. Aryl; Ar ² represents an extended aryl group having 6 to 25 carbon atoms; and each of A ¹ and A ² represents hydrogen, an aryl group having 6 to 25 carbon atoms or an alkane having 1 to 4 carbon atoms base.

In the above synthesis method, the metal catalyst is preferably a palladium catalyst.

One aspect of the invention is an anthracene derivative represented by structural formula (12).

Another aspect of the invention is an anthracene derivative represented by structural formula (20).

Another aspect of the invention is an anthracene derivative represented by the formula (43).

Another aspect of the invention is an anthracene derivative represented by the structural formula (16).

One aspect of the invention is a light-emitting element using the above-described anthracene derivative. In particular, the light-emitting element has the above-described anthracene derivative interposed between a pair of electrodes.

Another aspect of the present invention is a light-emitting element having a light-emitting layer interposed between a pair of electrodes, and the light-emitting layer has the above-described anthracene derivative. particular The above anthracene derivative is preferably used as a light-emitting substance. In other words, the light-emitting element preferably has a structure in which the above-described anthracene derivative emits light.

The present invention is characterized in that the light-emitting device has a light-emitting element including the above-described anthracene derivative and a controller for controlling the light-emitting element to emit light. The light-emitting device in this specification includes an image display device, a light-emitting device, and a light source (including a lighting device). Furthermore, the illuminating device also includes a mode in which a connector such as an FPC (Flexible Printed Circuit Board), a TAB (Tape-Rolled Automatic Coupling) tape or a TCP (tape-type carrier package) is connected to the flat plate; wherein the printed wiring board is A mode provided at the end of the TAP tape or TCP; and a mode in which the IC (integrated circuit) is directly mounted on the light-emitting device by a COG (Flosion-Crystalline) method.

Further, an electronic device using the light-emitting element of the present invention at a display portion is also included in the scope of the present invention. Therefore, the electronic device of the present invention has a display portion, and the display portion is provided with the above-described light-emitting element and a controller for controlling the light-emitting element to emit light.

According to the present invention, it is possible to omit the synthetic step for obtaining the target hydrazine derivative, and then it is possible to synthesize the hydrazine derivative more easily than usual. In addition, the time required for the reaction can be shortened, which leads to cost reduction. Further, according to the present invention, an anthracene derivative can be synthesized in a higher yield than conventionally.

The anthracene derivative of the present invention having a large band gap can emit light having a short wavelength. Further, the anthracene derivative can emit blue light having a high color purity.

A light-emitting element using the anthracene derivative of the present invention can emit a short wavelength Light and blue light with high color purity.

Further, a light-emitting material (hereinafter referred to as a dopant) having a smaller gap than the anthracene derivative of the present invention is added to a layer containing the anthracene derivative of the present invention, whereby light can be obtained from the dopant. . At this time, since the anthracene derivative of the present invention has an extremely large band gap, the anthracene derivative which is not derived from the present invention can be efficiently obtained, but the light from the dopant is doped even if light which emits light having a relatively short wavelength is used. When things are. In particular, by using a luminescent material having a wavelength of up to about 450 nm and exhibiting excellent blue purity as a dopant, a blue light-emitting element having high color purity can be obtained.

When a light-emitting element is produced in which the anthracene derivative of the present invention is added to a layer containing a material having a larger gap than the anthracene derivative (hereinafter referred to as a host), light derived from the anthracene derivative of the present invention can be obtained. In other words, the anthracene derivative of the present invention acts as a dopant. At this time, since the anthracene derivative has a large band gap and exhibits light having a short wavelength, a light-emitting element which can obtain blue light having high color purity can be manufactured.

When a luminescent material of the present invention containing an anthracene derivative is used, a luminescent material which provides excellent color purity in the form of blue light can be obtained. Further, when the luminescent material of the present invention containing an anthracene derivative is used, a highly reliable light-emitting element can be obtained.

The light-emitting element of the present invention containing the above anthracene derivative is a light-emitting element which can provide excellent color purity in a blue light form. Further, the light-emitting element of the present invention containing the above anthracene derivative is a highly reliable light-emitting element.

The light-emitting device of the present invention containing a light-emitting element is a light-emitting device having high color reproducibility. Furthermore, the light-emitting device of the invention containing the light-emitting element It is a highly reliable light-emitting device.

The electronic device of the present invention containing a light-emitting element is an electronic device having high color reproducibility. Furthermore, the electronic device of the present invention containing a light-emitting element is a highly reliable electronic device.

101‧‧‧Substrate

102‧‧‧first electrode

103‧‧‧ first floor

104‧‧‧ second floor

105‧‧‧ third floor

106‧‧‧ fourth floor

107‧‧‧Second electrode

301‧‧‧Substrate

302‧‧‧first electrode

303‧‧‧ first floor

304‧‧‧ second floor

305‧‧‧ third floor

306‧‧‧ fourth floor

307‧‧‧Second electrode

501‧‧‧first electrode

502‧‧‧Second electrode

511‧‧‧first lighting unit

512‧‧‧Second lighting unit

513‧‧‧ Charge generation layer

601‧‧‧ source drive circuit

602‧‧‧Pixel parts

603‧‧‧ brake drive circuit

604‧‧‧Seal substrate

605‧‧‧ sealing material

607‧‧‧ Space

608‧‧‧ lines

609‧‧‧Soft printed circuit board

610‧‧‧ element substrate

611‧‧‧Switching TFT

612‧‧‧ Current control

613‧‧‧ first electrode

614‧‧‧Insulator

616‧‧‧EL layer

617‧‧‧Second electrode

618‧‧‧Lighting elements

623‧‧‧n-channel TFT

624‧‧‧p-channel TFT

901‧‧‧Frame

902‧‧‧Liquid layer

903‧‧‧ Backlight

904‧‧‧Frame

905‧‧‧Drive IC

906‧‧‧ Terminal

951‧‧‧Substrate

952‧‧‧electrode

953‧‧‧Insulation

954‧‧‧Separation layer

955‧‧‧EL layer

956‧‧‧electrode

2001‧‧‧Frame

2002‧‧‧Light source

2101‧‧‧ glass substrate

2102‧‧‧first electrode

2103‧‧‧layers containing composite materials

2104‧‧‧ hole transport layer

2105‧‧‧Lighting layer

2106‧‧‧Electronic transport layer

2107‧‧‧Electronic injection layer

2108‧‧‧Second electrode

3001‧‧‧Lighting system

3002‧‧‧TV installation

9101‧‧‧Frame

9102‧‧‧ Support

9103‧‧‧ Display parts

9104‧‧‧ Horn parts

9105‧‧‧Video input terminal

9201‧‧‧ Subject

9202‧‧‧Frame

9203‧‧‧ Display parts

9204‧‧‧ keyboard

9205‧‧‧outer joint

9206‧‧‧ pointing device

9401‧‧‧ Subject

9402‧‧‧Frame

9403‧‧‧Display parts

9404‧‧‧Video input location

9405‧‧‧Video output location

9406‧‧‧ operation keys

9407‧‧‧outer joint

9408‧‧‧Antenna

9501‧‧‧ Subject

9502‧‧‧ Display parts

9503‧‧‧Frame

9504‧‧‧Outer joint

9505‧‧‧ Remote control receiving part

9506‧‧‧Image receiving site

9507‧‧‧Battery

9508‧‧‧Video input location

9509‧‧‧ operation keys

9510‧‧‧ eyepiece parts

1A to 1C are diagrams for explaining a light-emitting element of the present invention.

Fig. 2 is a view for explaining a light-emitting element of the present invention.

Fig. 3 is a view for explaining a light-emitting element of the present invention.

4A and 4B are diagrams for explaining a light-emitting device of the present invention.

5A and 5B are diagrams for explaining a light-emitting device of the present invention.

6A to 6D are diagrams respectively explaining an electronic device of the present invention.

Figure 7 is a diagram for explaining an electronic device of the present invention.

Figure 8 is a diagram for explaining the illumination system of the present invention.

Figure 9 is a diagram for explaining the illumination system of the present invention.

10A and 10B are graphs showing the ¹ H NMR of 9-[4-(N-carbazolyl)phenyl]-10-benzoquinone, respectively.

Figure 11 is a graph showing the absorption spectrum of a toluene solution of 9-[4-(N-carbazolyl)phenyl]-10-phenylhydrazine.

Figure 12 is a graph showing the absorption spectrum of a film of 9-[4-(N-carbazolyl)phenyl]-10-benzoquinone.

Figure 13 is a graph showing the emission spectrum of a toluene solution of 9-[4-(N-carbazolyl)phenyl]-10-benzoquinone.

Figure 14 is a graph showing 9-[4-(N-carbazolyl)phenyl]-10-benzoquinone The pattern of the emission spectrum of the film.

15A and 15B are graphs showing the ¹ H NMR of 9-(biphenyl-4-yl)-10-[4-(carbazol-9-yl)phenyl]fluorene, respectively.

Figure 16 is a graph showing the absorption spectrum of a toluene solution of 9-(biphenyl-4-yl)-10-[4-(carbazol-9-yl)phenyl]fluorene.

Figure 17 is a graph showing the absorption spectrum of a film of 9-(biphenyl-4-yl)-10-[4-(carbazol-9-yl)phenyl]fluorene.

Figure 18 is a graph showing the emission spectrum of a toluene solution of 9-(biphenyl-4-yl)-10-[4-(carbazol-9-yl)phenyl]fluorene.

Figure 19 is a graph showing the emission spectrum of a film of 9-(biphenyl-4-yl)-10-[4-(carbazol-9-yl)phenyl]fluorene.

20A and 20B are graphs showing the ¹ H NMR of 9-(4-t-butylphenyl)-10-[4-(carbazol-9-yl)]benzoquinone, respectively.

Figure 21 is a graph showing the absorption spectrum of a toluene solution of 9-(4-t-butylphenyl)-10-[4-(carbazol-9-yl)]phenylhydrazine.

Figure 22 is a graph showing the absorption spectrum of a film of 9-(4-t-butylphenyl)-10-[4-(carbazol-9-yl)]benzoquinone.

Figure 23 is a graph showing the emission spectrum of a toluene solution of 9-(4-t-butylphenyl)-10-[4-(carbazol-9-yl)]phenylhydrazine.

Figure 24 is a graph showing the emission spectrum of a film of 9-(4-t-butylphenyl)-10-[4-(carbazol-9-yl)]benzoquinone.

25A and 25B are graphs showing the ¹ H NMR of 9-[4-(carbazol-9-yl)phenyl]-10-(4-trifluoromethylphenyl)fluorene, respectively.

Figure 26 is a graph showing 9-[4-(carbazol-9-yl)phenyl]-10-(4-tri) A graph of the absorption spectrum of a toluene solution of fluoromethylphenyl) hydrazine.

Figure 27 is a graph showing the absorption spectrum of a film of 9-[4-(carbazol-9-yl)phenyl]-10-(4-trifluoromethylphenyl)fluorene.

Figure 28 is a graph showing the emission spectrum of a toluene solution of 9-[4-(carbazol-9-yl)phenyl]-10-(4-trifluoromethylphenyl)fluorene.

Figure 29 is a graph showing the emission spectrum of a film of 9-[4-(carbazol-9-yl)phenyl]-10-(4-trifluoromethylphenyl)fluorene.

30A and 30B are graphs showing the ¹ H NMR of 9-[4-(carbazol-9-yl)phenyl]-10-(2-naphthyl)anthracene, respectively.

Figure 31 is a graph showing the absorption spectrum of a toluene solution of 9-[4-(carbazol-9-yl)phenyl]-10-(2-naphthyl)anthracene.

Figure 32 is a graph showing the absorption spectrum of a film of 9-[4-(carbazol-9-yl)phenyl]-10-(2-naphthyl)anthracene.

Figure 33 is a graph showing the emission spectrum of a toluene solution of 9-[4-(carbazol-9-yl)phenyl]-10-(2-naphthyl)anthracene.

Figure 34 is a graph showing the emission spectrum of a film of 9-[4-(carbazol-9-yl)phenyl]-10-(2-naphthyl)anthracene.

Fig. 35 is a graph showing current density versus luminance characteristics of the light-emitting element manufactured in Concrete Example 6.

Fig. 36 is a graph showing the voltage versus luminance characteristics of the light-emitting element manufactured in the embodiment 6.

Fig. 37 is a graph showing the luminance versus current efficiency characteristics of the light-emitting element manufactured in Concrete Example 6.

38 is a view showing a light-emitting element manufactured in Embodiment 6. The spectrum of the emission spectrum.

Fig. 39 is a graph showing the current density versus luminance characteristics of the light-emitting element manufactured in Concrete Example 7.

Fig. 40 is a graph showing the voltage versus luminance characteristics of the light-emitting element manufactured in Concrete Example 7.

Fig. 41 is a graph showing the luminance versus current efficiency characteristics of the light-emitting element manufactured in Concrete Example 7.

Fig. 42 is a graph showing the emission spectrum of the light-emitting element manufactured in Specific Example 7.

Figure 43 is a graph showing the current density versus luminance characteristics of the light-emitting element manufactured in Concrete Example 8.

Fig. 44 is a graph showing the voltage versus luminance characteristics of the light-emitting element manufactured in the eighth embodiment.

Fig. 45 is a graph showing the luminance versus current efficiency characteristics of the light-emitting element manufactured in Concrete Example 8.

Fig. 46 is a graph showing the emission spectrum of the light-emitting element manufactured in Specific Example 8.

Figure 47 is a graph showing the current density versus luminance characteristics of the light-emitting element manufactured in Concrete Example 9.

Figure 48 is a graph showing the voltage versus luminance characteristics of the light-emitting element manufactured in Concrete Example 9.

Fig. 49 is a graph showing the luminance versus current efficiency characteristics of the light-emitting element manufactured in Concrete Example 9.

Figure 50 is a view showing a light-emitting element manufactured in Concrete Example 9. The spectrum of the emission spectrum.

Figure 51 is a graph showing the current density versus luminance characteristics of the light-emitting element manufactured in Concrete Example 10.

Figure 52 is a graph showing the voltage versus luminance characteristics of the light-emitting element manufactured in Concrete Example 10.

Figure 53 is a graph showing the luminance versus current efficiency characteristics of the light-emitting element manufactured in Concrete Example 10.

Fig. 54 is a graph showing the emission spectrum of the light-emitting element manufactured in Specific Example 10.

Figure 55 is a diagram for explaining a light-emitting element of a specific embodiment.

Figure 56 is a graph showing the results of CV measurement of the reducing end of 9-[4-(N-carbazolyl)phenyl]-10-phenylhydrazine.

Fig. 57 is a graph showing the results of CV measurement of the oxidation end of 9-[4-(N-carbazolyl)phenyl]-10-phenylhydrazine.

Figure 58 is a graph showing the results of CV measurement of the reducing end of 9-(biphenyl-4-yl)-10-[4-(carbazol-9-yl)phenyl]fluorene.

Figure 59 is a graph showing the results of CV measurement of the oxidation end of 9-(biphenyl-4-yl)-10-[4-(carbazol-9-yl)phenyl]fluorene.

Figure 60 is a graph showing the results of CV measurement of the reducing end of 9-(4-t-butylphenyl)-10-[4-(carbazol-9-yl)]phenylhydrazine.

Figure 61 is a graph showing the results of CV measurement of the oxidation end of 9-(4-t-butylphenyl)-10-[4-(carbazol-9-yl)]phenylhydrazine.

Fig. 62 is a graph showing the results of CV measurement of the reducing end of 9-[4-(N-carbazolyl)phenyl]-10-(4-trifluoromethylphenyl)fluorene.

Figure 63 is a graph showing the results of CV measurement of the oxidation end of 9-[4-(N-carbazolyl)phenyl]-10-(4-trifluoromethylphenyl)fluorene.

Fig. 64 is a graph showing the results of CV measurement of the reducing end of 9-[4-(N-carbazolyl)phenyl]-10-(2-naphthyl)anthracene.

Fig. 65 is a graph showing the results of CV measurement of the oxidation end of 9-[4-(N-carbazolyl)phenyl]-10-(2-naphthyl)anthracene.

Best mode for carrying out the invention

Hereinafter, specific mode modes of the present invention are described in detail with reference to the accompanying drawings. However, the present invention is not limited to the following description, and it is obvious to those skilled in the art that various changes and modifications may be made without departing from the scope and scope of the invention. Therefore, the present invention is not to be construed as being limited to the description of the specific embodiments.

(Specific embodiment mode 1)

This specific embodiment mode describes a method for synthesizing the anthracene derivative of the present invention.

In the method for synthesizing the anthracene derivative of the present invention, a 9-arylindole derivative having an active position at the 10-position and a 9-arylcarbazole derivative having an active position on the aryl group are used as a metal. The metal compound or the metal catalyst is coupled to synthesize the anthracene derivative represented by the formula (1).

More particularly, it will have an aryl group Ar ¹ at the 9-position and a 9-aryl fluorene derivative having an active position at the 10-position, and have an aryl group Ar ² at the 9-position and be active on the aryl group Ar ² . The 9-arylcarbazole derivative at a position is coupled with a metal, a metal compound or a metal catalyst to synthesize an anthracene derivative represented by the formula (1).

In other words, by coupling a hydrazine derivative represented by the general formula (2) with a carbazole derivative represented by the general formula (3) using a metal, a metal compound or a metal catalyst, a hydrazine represented by the general formula (1) can be synthesized. derivative.

In the general formulae (1) to (3), each of R ¹ to R ⁸ represents hydrogen, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms; and Ar ¹ represents having 6 to Aryl group of 25 carbon atoms; Ar ² represents an extended aryl group having 6 to 25 carbon atoms; and each of A ¹ and A ² represents hydrogen, an aryl group having 6 to 25 carbon atoms or has 1 to 4 An alkyl group of carbon atoms. Each of Ar ¹ , Ar ² , A ¹ and A ² may have a substituent. An alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen, a haloalkyl group, a cyano group, a nitro group, an ester group, an alkoxycarbonyl group, a decyloxy group, an alkoxy group can be provided. A group, a mercapto group, a decyl group, a hydroxyl group or the like is used as a substituent. In particular, the following may be mentioned: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, t-butyl, phenyl, o-tolyl, m-tolyl , p-tolyl, 1-naphthyl, 2-naphthyl, o-biphenyl, m-biphenyl, p-biphenyl, p-terphenyl-4-yl, p-terphenyl 3-yl, p-bitriphenyl-2-yl, m-triphenyl-4-yl, m-triphenyl-3-yl, m-triphenyl-2-yl, o-triphenyl- 4-yl, o-terphenyl-3-yl, o-triphenyl-2-yl, indol-2-yl, 9,9-dimethylinden-2-yl, 9,9-diphenyl Indole-2-yl, helix-9,9'-diin-2-yl, fluoro, chloro, bromo, iodo, trifluoromethyl, cyano, nitro, methyl, ethyl, methoxy Carbonyl, ethoxycarbonyl, ethoxylated, methoxy, ethoxy, carboxyl, ethyl, aldehyde or hydroxy.

Further, halogen, boric acid, organoboron, organotin, trifluoromethanesulfonate, Grignard reagent, organic mercury, thiocyanate, organozinc, organoaluminum, organozirconium or the like may be provided at each active site. X ³ and active position X ⁶ .

A metal such as copper or iron, a metal compound such as copper (I) iodide, a metal catalyst such as a palladium catalyst or a nickel catalyst may be provided as a metal, a metal compound or a metal catalyst for the reaction.

A method for synthesizing the anthracene derivative of the present invention is described in detail below. Anthracene derivative synthesized by the method of the present invention, X ³ makes it the 9-arylanthracene derivative (compound E) having an active position and an active position X ⁶ aryl group of the carbazole derivative 9- (Compound H) in The coupling reaction can be carried out by using a metal such as copper or iron or a metal compound such as copper (I) iodide, as shown in the synthetic scheme (A-4), which is a target compound. . The metal or metal compound may be a metal catalyst such as a palladium catalyst or a nickel catalyst. A Suzuki-Miyaura coupling, a Migita-Kosugi-Stille coupling, a Kumada-Tamao coupling, a Negishi coupling or the like can be used as the coupling reaction.

The 9-arylindole derivative (Compound E) having an active position X ³ can be synthesized by the following method. First, as shown in the synthetic scheme (A-1), an anthracene derivative (Compound A) (carbon at the 9-position, which is active, such as 9-fluorene halide) and an aromatic hydrocarbon having a reactive carbon (Compound B) (e.g., arylboronic acid) is obtained by coupling reaction using a metal such as copper or iron, a metal compound such as copper (I) iodide, or a metal catalyst such as a palladium catalyst or a nickel catalyst. Aryl hydrazine derivative (Compound C).

Next, as shown in the synthesis scheme (A-2), carbon at the 10-position is activated (for example, halogenation of a 9-aryl hydrazine derivative (compound C)), and 9 having an active position X ³ can be obtained. - an aryl hydrazine derivative (Compound E).

In the case where the 9-arylindole derivative (compound E) having an active position X ³ is 9-aryl-10-hydrazine halide or 9-aryl-10-trifluoromethanesulfonate oxime, the synthesis can be This is carried out by the method shown in the synthesis scheme (A-3). In particular, the carbon in the 9-position and the carbon-activated anthracene derivative (compound F) at the 10-position and the reactive carbon-aromatic (compound G) (such as arylboronic acid) are used, such as copper or iron. The metal-catalyzed coupling of a metal such as a copper (I) iodide metal compound such as a palladium catalyst or a nickel catalyst can obtain a 9-arylindole derivative (compound E) having an active position X ³ .

In the above schemes (A-1) to (A-4), each of R ¹ to R ⁸ represents hydrogen, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms; Ar ¹ Represents an aryl group having 6 to 25 carbon atoms; Ar ² represents an extended aryl group having 6 to 25 carbon atoms; and each of A ¹ and A ² represents hydrogen, an aryl group having 6 to 25 carbon atoms or has An alkyl group of 1 to 4 carbon atoms. Each of Ar ¹ , Ar ² , A ¹ and A ² may have a substituent. The substituent may be an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen, a haloalkyl group, a cyano group, a nitro group, a carbonyl group, an ester group, an alkoxy group or the like.

In the above schemes (A-1) to (A-4), each of X ¹ to X ⁶ represents halogen, boric acid, organoboron, organotin, trifluoromethanesulfonate, Grignard reagent, organic mercury, thiocyanate Acid ester, organozinc, organoaluminum or organozirconium.

Each synthesis process is described in detail below. Particular combinations of reactive sites (X ¹ to X ⁶ ) are specifically described. First, the synthesis scheme (A-4) will be described. When Suzuki-Miyaura coupling active position to X ³ of the 9-arylanthracene derivative (compound E) having an active position when the X ⁶ 9- aryl carbazole (Compound H) in a coupling reaction, such as synthetic scheme ( As represented by A-4), it is preferred that X ³ is halogen or trifluoromethanesulfonate and X ⁶ is boric acid or organic boron. Alternatively, it is preferred that X ³ is boric acid or organic boron and X ⁶ is halogen or trifluoromethanesulfonate. Moreover, a palladium catalyst is preferably used. When X ³ and X ⁶ are halogen, bromine or iodine is preferred, in other words, the synthesis method shown in the synthesis scheme (A-14a) or the synthesis scheme (A-14b) is preferred.

In the above schemes (A-14a) and (A-14b), each of R ¹ to R ⁸ represents hydrogen, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms; Ar ¹ Represents an aryl group having 6 to 25 carbon atoms; Ar ² represents an extended aryl group having 6 to 25 carbon atoms; and each of A ¹ and A ² represents hydrogen, an aryl group having 6 to 25 carbon atoms or has An alkyl group of 1 to 4 carbon atoms. Each of Ar ¹ , Ar ² , A ¹ and A ² may have a substituent. The substituent may be an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen, a haloalkyl group, a cyano group, a nitro group, a carbonyl group, an ester group, an alkoxy group or the like. X ¹³ and X ¹⁶ represent a halogen, and each of R ³¹ and R ³² represents an alkyl group having 1 to 6 carbon atoms. It should be noted that R ³¹ and R ³² combine to form a ring.

In the coupling reaction of a 9-arylindole derivative (compound E) having an active position X ³ with a 9-arylcarbazole having an active position X ⁶ (compound H), as in the synthetic scheme (A-4) Representative, an anthracene derivative (Compound I) having a very high yield can be obtained, which is the subject; therefore, Suzuki-Miyaura coupling is preferably carried out.

In the coupling reaction of a 9-arylindole derivative (compound E) having an active position X ³ with a 9-arylcarbazole having an active position X ⁶ (compound H), as represented by the synthetic scheme (A-4) When X ³ is a halogen, then X ⁶ is a Grignard reagent, organotin or organic mercury. The anthracene derivative (compound I) can be synthesized by performing a coupling reaction using a metal, a metal compound or a metal catalyst such as a palladium catalyst or a nickel catalyst. Alternatively, when X ⁶ is a halogen, then X ³ is a Grignard reagent, organotin or organic mercury. The indole derivative (compound I) can be synthesized by carrying out a coupling reaction using a metal, a metal compound or a metal catalyst such as a palladium catalyst or a nickel catalyst, which is the subject matter.

In the coupling reaction of a 9-arylindole derivative (compound E) having an active position X ³ with a 9-arylcarbazole having an active position X ⁶ (compound H), when X ³ and X ⁶ are halogen or sulfur In the case of a cyanate ester, the anthracene derivative (Compound I) which is the subject matter can be synthesized by a Ullmann reaction in which a copper or copper compound is used. In the example in which the Ullmann reaction is carried out, although X ³ and X ⁶ may be the same or different from each other, X ³ and X ^{6 are} preferably iodine.

Next, the synthesis scheme (A-1) will be described in detail. When Suzuki-Miyaura coupling is carried out in the synthesis of a 9-arylindole derivative (Compound C), as represented by the synthetic scheme (A-1), it is preferred that X ¹ is a halogen or a trifluoromethanesulfonate. And X ² is boric acid or organic boron. For example, 9-aryl-10-hydrazine halide and (carbazol-9-yl)arylboronic acid are preferably used. Alternatively, it is preferred that X ¹ is boric acid or organic boron and X ² is halogen or trifluoromethanesulfonate. Further, a palladium catalyst is preferably used. When X ¹ and X ² are halogen, bromine or iodine is preferred, in other words, the synthesis scheme (A-1) is preferably a synthetic scheme (A-11a) or a synthetic scheme (A-11b).

In the above schemes (A-11a) and (A-11b), each of R ¹ to R ⁸ represents hydrogen, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms; and Ar ¹ represents an aryl group having 6 to 25 carbon atoms. Ar ¹ may have a substituent. The substituent may be an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen, a haloalkyl group, a cyano group, a nitro group, a carbonyl group, an ester group, an alkoxy group or the like. X ¹¹ and X ¹² represent a halogen, and each of R ¹¹ and R ¹² represents an alkyl group having 1 to 6 carbon atoms. It should be noted that R ¹¹ and R ¹² combine to form a ring.

In the synthesis of the 9-arylindole derivative (Compound C) represented by the synthetic scheme (A-1), a 9-arylindole derivative (Compound C) having a very high yield, which is a target substance, can be obtained; Therefore, Suzuki-Miyaura coupling is preferably carried out. In particular, the ease of the synthetic material is considered, so it is preferred that X ¹ is a halogen or a trifluoromethanesulfonate and X ² is a boric acid or an organic boron.

When X ¹ is a halogen, then X ² is a Grignard reagent, organotin, organomercury, boric acid or organoboron. The 9-arylindole derivative (Compound C) can be synthesized by performing a coupling reaction using a metal, a metal compound or a metal catalyst such as a palladium catalyst or a nickel catalyst. Alternatively, when X ² is a halogen, then X ¹ is a Grignard reagent, organotin, organomercury, boric acid or organoboron. The 9-arylindole derivative (Compound C) can be synthesized by performing a coupling reaction using a metal, a metal compound or a metal catalyst such as a palladium catalyst or a nickel catalyst.

When X ¹ and X ² are halogen or thiocyanate, the anthracene derivative (compound A) and the aromatic hydrocarbon having a reactive carbon (compound B) are coupled by a Ullmann reaction using a copper or copper compound. Synthesis of a 9-arylindole derivative (Compound C). In the example in which the Ullmann reaction is carried out, although X ¹ and X ² may be the same or different from each other, X ¹ and X ^{2 are} preferably iodine.

Next, the synthesis scheme (A-2) will be described in detail. The carbon at the 10-position is activated, such as the halogenation of the 9-arylindole derivative (compound C) represented by the synthetic scheme (A-12), and the 9-aryl group having the active position X ³ can be obtained. Anthracene derivative (Compound E). When bromination is carried out in the halogenation reaction, bromination can be carried out using bromine, N-bromosuccinimide (NBS) or the like. Alternatively, when iodination is carried out, iodination can be carried out using iodine, properiodate, potassium iodide, N-iodosuccinimide or the like.

Next, the synthesis scheme (A-3) will be described in detail. When Suzuki-Miyaura coupling is carried out in the reaction represented by the synthesis scheme (A-3), it is preferred that X ⁴ is halogen or trifluoromethanesulfonate and X ⁵ is boric acid or organic boron. Alternatively, it is preferred that X ⁴ is boric acid or organic boron and X ⁵ is halogen or trifluoromethanesulfonate. Further, a palladium catalyst is preferably used. When X ⁴ and X ⁵ are halogen, bromine or iodine is preferred.

In other words, when the aryl hydrazine derivative (compound E) having the active position X ³ is a 9-aryl-10-hydrazine halide having a trifluoromethanesulfonate group at the 10-position as a reactive site or 9 - in the case of ruthenium, 9,10-dihalogenated ruthenium (compound F) and arylboronic acid (compound G) can be synthesized by a coupling reaction using a palladium catalyst or the like at a molar ratio of 1:1, such as synthesis. Represented by process (A-13a). Meanwhile, the arylboronic acid (Compound G) may be an aryl organoboron compound. Alternatively, hydrazine-9,10-diboronic acid (compound F) and a halogenated aromatic hydrocarbon (compound G) are coupled using a palladium catalyst or the like at a molar ratio of 1:1, as represented by the synthetic scheme (A-13b). , 9-aryl-10-oxime halide can be synthesized. Meanwhile, -9,10-diboronic acid (Compound F) may be a ruthenium-9,10-diorgano boron compound.

In the above schemes (A-13a) and (A-13b), each of R ¹ to R ⁸ represents hydrogen, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms; and Ar ¹ represents an aryl group having 6 to 25 carbon atoms. Ar ¹ may have a substituent. The substituent may be an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen, a haloalkyl group, a cyano group, a nitro group, a carbonyl group, an ester group, an alkoxy group or the like. X ¹³ , X ¹⁴ and X ¹⁵ represent a halogen, and each of R ²¹ and R ²² represents an alkyl group having 1 to 6 carbon atoms. It should be noted that R ²¹ and R ²² combine to form a ring.

Very high yield can be obtained by coupling a carbon at the 9-position and a carbon-activated anthracene derivative (compound F) at the 10-position with an aromatic hydrocarbon (compound G) having a reactive carbon. The subject matter is represented by the synthetic scheme (A-3); therefore, Suzuki-Miyaura coupling is preferably carried out. In particular, the ease of the synthetic material is considered, so it is preferred that X ⁶ is a halogen or a trifluoromethanesulfonate and X ⁴ is a boric acid or an organic boron.

When X ⁴ is a halogen, then X ⁵ is a Grignard reagent, organotin, organomercury, boric acid or organoboron. The 9-arylindole derivative (compound E) can be synthesized by performing a coupling reaction using a metal, a metal compound or a metal catalyst such as a palladium catalyst or a nickel catalyst. Alternatively, when X ⁵ is a halogen, then X ⁴ is a Grignard reagent, organotin, organomercury, boric acid or organoboron. By carrying out a coupling reaction using a metal, a metal compound or a metal catalyst such as a palladium catalyst or a nickel catalyst. A 9-arylindole derivative (Compound E) can be synthesized.

When X ⁴ and X ⁵ are halogen or thiocyanate, the carbon at the 9-position and the carbon at the 10-position are activated with an anthracene derivative (compound F) and an aromatic hydrocarbon having a reactive carbon ( Compound G) can be coupled by Ullmann reaction using copper or a copper compound. In the example in which the Ullmann reaction is carried out, although X ⁴ and X ⁵ may be the same or different from each other, X ⁴ and X ^{5 are} preferably iodine.

According to the above synthesis method, an anthracene derivative represented by the formula (1) can be synthesized. In other words, different substituents are each introduced into the 9-position and 10-position of the anthracene skeleton.

In the case of compounds in which different substituents are synthesized and introduced into the 9-position and 10-position of the anthracene skeleton, the skeletons are usually coupled one after another; thus increasing the number of steps is not suitable for industrial use. In other words, the time taken for the synthesis becomes longer, and the cost is increased by lowering the yield and the like. However, when as many steps as possible are omitted (for example, in the case where the two skeletons are simultaneously introduced into the anthracene skeleton in one stage), it is expected that various by-products are produced and it is difficult to purify; therefore, it is not suitable for the industry. In particular, since the purity of the organic semiconductor material is extremely important, when it is difficult to purify, there is a risk that the material properties are greatly lowered.

In the synthesis method of the present invention, the skeleton to be introduced into the anthracene skeleton is separately synthesized, and the skeleton is introduced into the 9-position and the 10-position in 1 to 2 steps in 1 to 3 steps. In the synthesis method of the present invention, the reaction is carried out in a high yield at each stage, and the generation of by-products is suppressed; therefore, when considering the above problems, the method can be regarded as the most suitable method. In addition, the method is suitable for a large amount of synthesis because by-products can be suppressed and can be regarded as a method suitable for industrial use.

Further, the synthesis stage for obtaining an anthracene derivative (this is the subject matter) can be omitted, and an anthracene derivative having a higher purity can be synthesized more easily than a conventional method. In addition, the time period of the reaction can be shortened, which leads to cost reduction.

(Specific embodiment mode 2)

The anthracene derivatives of the present invention are described in this particular embodiment mode.

The anthracene derivative of the present invention is an anthracene derivative represented by the formula (1).

The 9- and 10-position fluorene skeleton of the anthracene derivative represented by the general formula (1) is introduced into an aryl group as a substituent.

Usually, because of the high color purity, the blue light-emitting material has low electricity. Since chemical stability and low excited state stability are achieved, it is difficult to have a long life using a light-emitting element that emits a blue light-emitting material. Therefore, the electrochemical stability and the excited state stability of a blue light-emitting material having high color purity are required to improve the reliability of a light-emitting element using a blue light-emitting material. Further, in the light-emitting element and in the light-emitting device and the electronic device having the light-emitting element, stability against high temperature is particularly required in consideration of various external environments in which the element and the device are used.

Anthracene derivatives are known as compounds capable of emitting blue light; however, ruthenium itself tends to form solid excimers; therefore, it is impossible to obtain effective luminescence even in the case where ruthenium itself is used for a light-emitting element. Furthermore, the chromaticity is reduced. Therefore, it is necessary to introduce large substituents to avoid the formation of excimers. In particular, an advantageous method is to introduce substitutions based on the 9- and 10-positions, which are the most reactive sites for hydrazine. Further, in order to maintain the high carrier transport property of the anthracene skeleton, it is particularly effective to introduce an aryl group. The anthracene derivative represented by the formula (1) can suppress the formation of an excimer because the 9- and 10-positions of the anthracene skeleton of the anthracene derivative are introduced into the aryl group as a substituent. Furthermore, the carrier transport properties can be maintained.

On the other hand, the carbazolyl group has a structure in which a phenyl group of a diphenylamine group is bridged, so that the compound containing a carbazolyl group has higher thermal stability than a compound containing a diphenylamine group. Therefore, the thermal stability (glass transition temperature or melting point) of the compound can be improved by introducing a carbazolyl group. Further, the inventors have revealed that in the case of using a compound in which one carbazolyl group is introduced, for example, a compound in which a carbazolyl group is introduced only in one phenyl group of diphenylphosphonium, the electrochemical stability is increased. Introducing carbazole groups in two The compounds of the two phenyl groups of phenylhydrazine are higher.

In other words, the inventors have revealed that electrochemical stability is greatly improved by introducing the carbazolyl group only into the aryl group at one end. Accordingly, the present invention is characterized in that the anthracene derivative has an aryl group as a substituent at one of the 9- and 10-positions of fluorene and an aryl group having a carbazole group at another position. Further, the carbazolyl group preferably has a structure in which a nitrogen atom at the 9-position is directly coupled to the aryl group.

The anthracene derivative of the present invention having the above structure has an extremely large band gap; therefore, light emission having a short wavelength is possible, and blue light having high color purity can be obtained.

It should be noted that in the anthracene derivatives provided by the present invention, an aryl group or an alkyl group may be included in the anthracene skeleton or an aryl group directly coupled with the anthracene skeleton. This is based on the following reasons.

In a light-emitting element, material crystallization causes a capital loss of the element. In particular, this is a direct cause of a short circuit between electrodes, which suppresses luminescence. therefore. It is necessary to reduce the crystallinity of the material. In this regard, it is effective to introduce an appropriate substituent into the anthracene skeleton or an aryl group directly coupled to the anthracene skeleton. An aryl group or an alkyl group can be used as the substituents.

The aryl group or alkyl group to be introduced is not limited; however, a phenyl group, an o-biphenyl group or the like is preferred as the aryl group, and a methyl group, a tert-butyl group or the like is preferably used as the alkyl group.

The alkyl group has an extremely large crystallization inhibiting effect, and can suppress crystallization of a structure which cannot suppress crystallization by introducing an aryl group. It should be noted that the introduction of an alkyl group may reduce the carrier transport properties; therefore, the crystallinity of the substance to which the substituent is to be introduced In a less high case, it is more effective to use an aryl group as a substituent to be introduced in order to maintain the carrier transport property.

Typical examples of the anthracene derivatives of the present invention represented by the above formula (1) are shown in the following structural formulae (11) to (53), structural formulae (61) to (76), and structural formulas (81) to (90). in. Of course, the invention is not limited thereto.

The anthracene derivatives of the invention have high electrochemical stability. Further, the anthracene derivative of the present invention has high thermal stability. Further, the anthracene derivative of the present invention has an extremely large band gap; therefore, when used as a main body in the light-emitting layer of the light-emitting element, blue light having high color purity can be obtained. Further, the anthracene derivative of the present invention has an extremely large band gap; therefore, when used as a dopant in the light-emitting layer of the light-emitting element, blue light having high color purity can be obtained. The light-emitting element using the anthracene derivative according to the present invention can have high reliability. Particularly when the ruthenium derivative of the present invention is used as a host and a dopant in the light-emitting layer of the light-emitting element, a light-emitting element having extremely high reliability can be obtained.

The anthracene derivatives represented by the above structural formulas (11) to (53), structural formulae (61) to (76) and structural formulas (81) to (90) can be synthesized as described in the specific embodiment mode 1. Method synthesis.

(Specific embodiment mode 3)

The mode of the light-emitting element using the anthracene derivative of the present invention is described in this embodiment mode with reference to Figs. 1A to 1C and Fig. 2.

The light-emitting element of the present invention has several layers between a pair of electrodes. The number of layers is obtained by stacking layers formed of substances having high carrier injection properties or substances having high carrier transport properties, so that the light-emitting region is formed at a position separate from the electrodes, in other words, the carrier is The parts separated from the electrodes are recombined. In the specification of the present invention, a plurality of layers formed between a pair of electrodes are referred to herein as EL layers.

In this embodiment mode, the illuminating element comprises a plurality of successively stacked An electrode 102, a first layer 103, a second layer 104, a third layer 105, a fourth layer 106, and a second electrode 107. It should be noted that this particular embodiment mode is described below under the condition that the first electrode 102 acts as an anode and the second electrode 107 acts as a cathode.

The substrate 101 is used as a support substrate for a light-emitting element. A substrate 101 such as glass, plastic or the like can be used. It should be noted that other materials may be used as long as they serve as a support substrate in the manufacturing method of the light-emitting element.

As the first electrode 102, a metal, an alloy, a conductive compound, a mixture thereof or the like having a high work function (especially 4.0 eV or higher) is preferably used. In particular, indium oxide-tin oxide (ITO: indium tin oxide), indium oxide-tin oxide containing antimony or antimony oxide, indium oxide-zinc oxide (IZO: indium zinc oxide), indium oxide containing tungsten oxide and zinc oxide can be used. (IWZO) or the like. Although the conductive metal oxide thin films are usually formed by sputtering, they may be formed by applying a sol-gel method or the like. For example, an indium oxide-zinc oxide (IZO) film can be formed by a sputtering method using a target in which 1 to 20% by weight of zinc oxide is added to indium oxide. An indium oxide (IWZO) film containing tungsten oxide and zinc oxide can be formed by a sputtering method using 0.5 to 5% by weight of tungsten oxide and 0.1 to 1% by weight of zinc oxide included in the indium oxide. target. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium may be provided. (Pd), a nitride of a metal material (such as titanium nitride: TiN) or the like.

The first layer 103 is a layer containing a substance having high hole injection properties. Molybdenum oxide (MoO _X ), vanadium oxide (VO _X ), ruthenium oxide (RuO _X ), tungsten oxide (WO _X ), manganese oxide (MnO _X ) or the like can be used. Alternatively, the first layer 103 may use phthalocyanine (abbreviation: H ₂ Pc); a compound mainly composed of phthalocyanine, such as sassafras bronze (abbreviation: CuPc); an aromatic amine compound such as 4, 4'-double [N-(4-Diphenylaminophenyl)-N-anilino]biphenyl (abbreviation: DPAB) or 4,4'-bis(N-{4-[N-(3-methylphenyl)-N- Anilino]phenyl}-N-anilinobiphenyl (abbreviation: DNTPD); or a polymeric material such as poly(ethylenedioxythiophene)/poly(styrenesulfonic acid) (PEDOT/PSS) or the like Object formation.

Alternatively, a composite material formed by combining an organic compound and an inorganic compound may be used for the first layer 103. In particular, a composite material containing an organic compound and an inorganic compound has an electron accepting property with respect to an organic compound, and has excellent hole injection properties and hole transport properties because electrons are transferred between an organic compound and an inorganic compound, and Increase the carrier density.

In the example in which the composite material formed by combining the organic compound and the inorganic compound is used in the first layer 103, the first layer 103 can achieve ohmic contact with the first electrode 102; therefore, the selection of the first electrode material is not relevant. Work function.

An oxide of a transition metal is preferably used as the inorganic compound for the composite material. Further, an oxide of a metal of Groups 4 to 8 of the periodic table can be used. In particular, it is preferred to use vanadium oxide, cerium oxide, cerium oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide and cerium oxide because of their high electron accepting properties. Among them, molybdenum oxide is particularly preferred because it is stable under air, has low hygroscopic properties and is easy to handle.

As the organic compound for the composite material, various compounds such as an aromatic amine oxygen compound, a carbazole derivative, an aromatic hydrocarbon, and a polymer compound such as an oligomer, a dendrimer or a polymer can be used. The organic compound used for the composite material is preferably an organic compound having high hole transport properties. In particular, a substance having a hole mobility of greater than or equal to 10 ^-6 cm 2 /volt second is preferably used. However, other materials than those may be used as long as their hole transport properties are greater than their electron transport properties. Organic compounds which can be used in composite materials are particularly shown below.

For example, the following may be used as the aromatic amine compound: N,N'-bis(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-double [N-(4-Diphenylaminophenyl)-N-anilino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N-(3-toluidine)-N- Anilino]phenyl}-N-anilino)biphenyl (abbreviation: DNTPD), 1,3,5-gin[N-(4-diphenylaminophenyl)-N-anilino]benzene (abbreviation: DPA3B ) and the like.

In particular, the following can be used as a carbazole derivative which can be used for a composite material: 3-[N-(9-phenyloxazol-3-yl)-N-anilino]-9-phenylcarbazole (abbreviation: PCzPCA1) ,3,6-bis[N-(9-phenyloxazol-3-yl)-N-anilino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl) -N-(9-phenyloxazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1); and the like.

In addition, the following can be used as the carbazole derivative which can be used for the composite material: 4,4'-bis(N-carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-gin [4-(N- Carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(N- Benzazolyl)]phenyl-10-benzoquinone (abbreviation: CzPA), 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene; Or similar.

For example, the following can be used as an aromatic hydrocarbon which can be used for a composite material: 2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA); 2-tert-butyl-9, 10-bis(1-naphthyl)anthracene; 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA); 2-tert-butyl-9,10-bis(4-benzene Phenyl phenyl) hydrazine (abbreviation: t-BuDBA); 9,10-bis(2-naphthyl) fluorene (abbreviation: DNA); 9,10-diphenylhydrazine (abbreviation: DPAnth); 2-third butyl (abbreviation: t-BuAnth); 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA); 2-tert-butyl-9,10-bis[2-(1-naphthalene) Phenyl]anthracene; 9,10-bis[2-(1-naphthyl)phenyl]anthracene; 2,3,6,7-tetramethyl-9,10-di(1-naphthyl)anthracene ; 2,3,6,7-tetramethyl-9,10-di(2-naphthyl)anthracene; 9,9'-binaphthyl;10,10'-diphenyl-9,9'-binaphthyl10,10'-bis(2-phenylphenyl)-9,9'-binaphthyl;10,10'-bis[(2,3,4,5,6-pentaphenyl)phenyl]-9,9'-binaphthyl;anthracene;tetracycline; red fluorene; anthracene; 2,5,8,11-tetra(t-butyl)anthracene and the like. In addition to these compounds, pentacyclin, coronene or the like can also be used. In particular, it is more preferable to have a hole mobility of 10 ^-6 cm 2 /volt second or more and an aromatic hydrocarbon having 10 to 42 carbon atoms.

The aromatic hydrocarbons useful in the composite may have a vinyl skeleton. For example, the following may be used as the aromatic hydrocarbon having a vinyl group: 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviation: DPVBi); 9,10-bis[4-(2,2) -Diphenylvinyl)phenyl]indole (abbreviation: DPVPA); and analogs.

Moreover, a polymer compound such as poly(N-vinyl anthracene) can also be used. Oxazole) (abbreviation: PVK) or poly(4-vinyltriphenylamine) (abbreviation: PVTPA).

As the substance forming the second layer 104, a substance having a high hole transport property is preferable, particularly an aromatic amine compound (i.e., a compound having a benzene ring-nitrogen bond). 4,4'-bis[N-(3-tolyl)-N-anilino]biphenyl, a derivative thereof such as 4,4'-bis[N-(1-naphthyl)-N-aniline can be used. Biphenyl (hereinafter referred to as NPB) and starburst aromatic amine compounds such as 4,4',4"-parade (N,N-diphenylamino)triphenylamine and 4,4',4"- [N-(3-Tolyl)-N-anilino]triphenylamine is widely used as a material. The materials described herein are primarily materials having a mobility of holes greater than or equal to ^10-6 square centimeters per volt second, respectively. However, other materials than the compounds may be used as long as their hole transport properties are greater than their electron transport properties. The second layer 104 is not limited to a single layer, and a mixed layer of the foregoing substances or a stacked layer having two or more layers each containing the foregoing substances may be used.

The third layer 105 is a layer containing a luminescent substance. In this embodiment mode, the third layer 105 comprises the anthracene derivative of the present invention as described in the specific embodiment mode 1. The anthracene derivative of the present invention can be favorably applied as a luminescent substance to a light-emitting element because the anthracene derivative of the present invention can emit light having a short wavelength and exhibit blue light having a high color purity.

As the fourth layer 106, a substance having high electron transport properties can be used. For example, a layer containing a metal complex or the like having a quinoline or benzoquinoline skeleton such as ginseng (8-quinoline) complex aluminum (abbreviation: Alq), ginseng (4-methyl-8-) may be used. Quinoline) aluminum (abbreviation: Almq ₃ ), bis(10-hydroxybenzo[h]quinoline) oxime (abbreviation: BeBq ₂ ) or bis(2-methyl-8-quinoline) (4-benzene) Alkyl phenol) aluminum (abbreviation: BAlq). Alternatively, a metal complex or the like having a oxazole-based or thiazole-based ligand such as bis[2-(2-hydroxyphenyl)benzoxazole] complex zinc (abbreviation: Zn) may be used. (BOX) ₂ ) or bis[2-(2-hydroxyphenyl)benzothiazole] complex zinc (abbreviation: Zn(BTZ) ₂ ). In addition to the metal complex, 2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1, can also be used. 3-bis[5-(p-t-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenyl)-4 -Phenyl-5-(4-t-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), diphenylmorpholine (abbreviation: BPhen), bathocuproine (abbreviation: BCP) or the like. The materials described herein are primarily those having a mobility of holes greater than or equal to 10 ^-6 cm 2 / volt second, respectively. The electron transport layer may be formed using other materials than those described above as long as the material has higher electron transport properties than hole transport properties. Further, the electron transport layer is not limited to a single layer, and each of the layers may be stacked in two or more layers made of the foregoing substances.

As the material forming the second electrode 107, a metal, an alloy, a conductive compound, a mixture thereof or the like having a low work function (especially 3.8 eV or less) is preferably used. An element belonging to Group 1 or Group 2 of the periodic table may be used, that is, an alkali metal such as lithium (Li) or cesium (Cs), an alkaline earth metal such as magnesium (Mg), calcium (Ca) or strontium (Sr). An alloy containing these metals (MgAg, AlLi) is a special example of the cathode material. a rare earth metal such as Eu (Eu) or Yb (Yb) containing such rare earths Metal alloys or the like are also suitable. However, by providing a layer having a function of promoting electron injection between the second electrode 107 and the fourth layer 106, it is possible to stack with the second electrode, and various conductive materials such as Al, Ag, ITO or contain germanium or The ITO of yttria can be used for the second electrode 107 regardless of the size of the work function.

An alkali metal, an alkaline earth metal or a compound thereof such as lithium fluoride (LiF), cesium fluoride (CsF) or calcium fluoride (CaF ₂ ) can be used as the layer having a function of promoting electron injection. For example, a layer containing a substance having electron transporting property and an alkali metal, an alkaline earth metal or a compound thereof (for example, Alq including magnesium (Mg)) may be used. It is preferable to use the layer because the electron injection from the second electrode 107 is efficiently performed.

The first layer 103, the second layer 104, the third layer 105, and the fourth layer 106 can be formed using various methods. For example, an evaporation method, an inkjet method, a spin coating method, or the like can be used. Further, each electrode or each layer may be formed by a different film formation method.

Since a different potential is generated between the first electrode 102 and the second electrode 107, current flows, so that holes and electrons recombine in the third layer of the substance having high luminescent properties, which results in luminescence from the present invention. The illumination of the component. In other words, the light-emitting element of the present invention has a structure in which the light-emitting region is formed in the third layer 105.

The illumination is extracted outward through one or both of the first electrode 102 and the second electrode 107. Therefore, one or both of the first electrode 102 and the second electrode 107 are formed using an electrode having light transmitting properties. An example in which only the first electrode 102 is an electrode having optical transmission properties The light emission is extracted from the substrate surface via the first electrode 102 as shown in FIG. 1A. Alternatively, in the example in which only the second electrode 107 is an electrode having light transmitting properties, the light emitting system is extracted from the reverse side of the substrate via the second electrode 107 as shown in FIG. 1B. In an example in which both the first electrode 102 and the second electrode 107 are electrodes having optical transmission properties, the luminescence is extracted from both the substrate surface and the reverse side of the substrate via the first electrode 102 and the second electrode 107. Out, as shown in Figure 1C.

The structure of the layer provided between the first electrode 102 and the second electrode 107 is not limited to the above structure. A structure other than the above structure may be used as long as the light-emitting region in which the hole and the electron recombines are located away from the first electrode 102 and the second electrode 107 to prevent quenching due to the vicinity of the light-emitting region and the metal.

In other words, the stacked structure of the layers is not particularly limited to the above structure, and a substance having high electron transporting property, a substance having high hole transporting property, a substance having high electron injecting property, a substance having high hole injecting property, A layer formed of a bipolar substance (a substance having high electron transport properties and high hole transport properties), a hole blocking material or the like can be freely combined with the anthracene derivative of the present invention.

The light-emitting element shown in Fig. 2 has a first electrode 302 serving as a cathode, a first layer 303 formed using a substance having high electron transporting property, a second layer 304 containing a light-emitting substance, and having a high hole transmission. The third layer 305 formed of the substance of the nature, the fourth layer 306 formed using a substance having high electron injecting property, and the second electrode 307 serving as an anode are successively stacked on the substrate 301.

In this embodiment mode, the light-emitting elements are fabricated on a substrate made of glass, plastic or the like. Passive matrix light-emitting devices can be fabricated by fabricating a plurality of the above-described light-emitting elements on a single substrate. Alternatively, for example, a thin film transistor (IFT) may be formed on a substrate made of glass, plastic or the like, and a light-emitting element may be fabricated on an electrode electrically connected to the TFT. Therefore, an active matrix light-emitting device can be manufactured in which the driving of the light-emitting elements is controlled by the TFT. The structure of the TFT is not strictly limited, and the TFT may be a staggered TFT or an inverted staggered TFT. The crystallinity of the semiconductor used for the TFT is also not limited, and an amorphous semiconductor or a crystalline semiconductor can be used. Further, the driving circuit formed on the TFT substrate may be formed using an N-type TFT and a P-type TFT, or may be formed using any of an N-type TFT and a P-type TFT.

As shown in this specific embodiment mode, the anthracene derivative of the present invention can be used for the light-emitting layer, as shown in the embodiment mode, without adding any other light-emitting substance because the anthracene derivative emits high-purity blue light. .

Since the anthracene derivative of the present invention has high luminous efficiency, a light-emitting element having high luminous efficiency can be obtained by using the anthracene derivative of the present invention in a light-emitting element. A light-emitting element having high reliability can also be obtained by using the anthracene derivative of the present invention in a light-emitting element.

Since the light-emitting element using the anthracene derivative of the present invention can emit blue light having high color purity, it can be advantageously used for a full-color display. Furthermore, the use of the luminescent element of the hydrazine derivative of the present invention to achieve the ability to emit blue light with high reliability allows its use in full color displays.

(Specific embodiment mode 4)

A light-emitting element having a structure different from that shown in the embodiment mode 3 is described in this embodiment mode.

The third layer 105 shown in the specific embodiment mode 3 formed has a structure in which the anthracene derivative of the present invention is dispersed in another substance, whereby the luminescence from the anthracene derivative of the present invention can be obtained. Since the anthracene derivative of the present invention exhibits blue light having high color purity, a blue light-emitting element exhibiting high color purity can be obtained.

Here, a substance having a larger gap than the anthracene derivative of the present invention is preferably used as a substance for dispersing the anthracene derivative of the present invention. In particular, low molecular compounds such as 4,4',4"-tris(N-carbazolyl)triphenylamine (abbreviation: TCTA), 1,1-bis[4-(diphenylamino)phenyl]cyclohexane can be used. Alkane (abbreviation: TPAC), 9,9-bis[4-(diphenylamino)phenyl]anthracene (abbreviation: TPAF), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP) , 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 2,2', 2"- (1,3,5-benzenetriyl) ginseng (1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 3-(4-t-butylphenyl)-4-phenyl-5-( 4-biphenyl)-1,2,4-triazole (abbreviation: TAZ), or a polymer compound such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA) or poly(2,5-pyridinediyl) (abbreviation: PPy).

Since the anthracene derivative of the present invention can emit blue light having high color purity by using an anthracene derivative for a light-emitting element, a blue-emitting light-emitting element exhibiting high color purity can be obtained.

Since the anthracene derivative of the present invention has high luminous efficiency, a light-emitting element having high luminous efficiency can be obtained by using the anthracene derivative of the present invention in a light-emitting element. A light-emitting element having high reliability can also be obtained by using the anthracene derivative of the present invention in a light-emitting element.

Since the light-emitting element using the anthracene derivative of the present invention can emit blue light having high color purity, it can be advantageously used for a full-color display. Furthermore, the use of the luminescent element of the hydrazine derivative of the present invention to achieve the ability to emit blue light with high reliability allows its use in full color displays.

It should be noted that the structure shown in the specific embodiment mode 2 can be used as appropriate, except for the third layer 105.

(Specific embodiment mode 5)

A light-emitting element having a structure different from that shown in the specific embodiment modes 3 and 4 is described in this embodiment mode.

The third layer 105 shown in the specific embodiment mode 3 formed has a structure in which a luminescent substance is dispersed in the hydrazine derivative of the present invention, whereby luminescence from the luminescent substance can be obtained.

In the example in which the anthracene derivative of the present invention is used as a material for dispersing another luminescent material, the luminescent color obtained from the luminescent material can be obtained. Further, mixed luminescence obtained from the anthracene derivative of the present invention and the luminescent material dispersed in the anthracene derivative can also be obtained.

Here, a substance having a band gap smaller than that of the anthracene derivative of the present invention is preferably used as a luminescent substance dispersed in the anthracene derivative of the present invention. In particular, the following materials can be provided, such as N,N'-bis[4-(9H-carbazol-9-yl)benzene -N,N'-diphenylindole-4,4'-diamine (abbreviation: YGA2S), 2,5,8,11-tetra(t-butyl)anthracene (abbreviation: TBP), hydrazine, Coumarin 30, coumarin 6, coumarin 545T, N, N'-dimethyl quinacridone (abbreviation: DMQd), N, N'-diphenylquinacridone (abbreviation: DPQd) , N,N,9-triphenylphosphonium-9-amine (abbreviation: DPhAPhA), 5,12-bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetracycline (abbreviation :BPT), erythritol, N,N,N',N'-indole (4-methylphenyl)tetracycline-5,11-diamine (abbreviation: p-mPhTD) or 7,13-diphenyl-N , N, N', N'-肆(4-methylphenyl)indeno[1,2-a]fluorescein-3,10-diamine (abbreviation: p-mPhAFD).

Since the anthracene derivative of the present invention has a large band gap, the luminescent substance dispersed in the anthracene derivative of the present invention is selected from a wide range of selection. For example, a blue-emitting luminescent substance having high color purity can be dispersedly exhibited. In particular, a luminescent substance having a band gap of 2.7 eV or more and 3.0 eV or less or a luminescent substance having a maximum luminescent wavelength of between 400 and 500 nm is dispersed in the hydrazine derivative of the present invention because The luminescent substance exhibits blue light having high color purity, whereby a blue light-emitting element exhibiting high color purity can be obtained.

It should be noted that the structure shown in the specific embodiment mode 3 can be used as appropriate, except for the third layer 105.

(Specific embodiment mode 6)

Light-emitting elements having a structure different from those shown in the specific embodiment modes 3 to 5 are described in this embodiment mode.

By combining the anthracene derivatives of the invention with the derivatives of the invention The inorganic compound of the electron accepting property of the living body can be used for the layer containing the anthracene derivative of the present invention between the anode and the light-emitting layer. A layer containing especially an anthracene derivative can be used for the first layer 103 or the second layer 104 shown in the embodiment mode 3. The carrier density is increased by the use of such composite materials, which contributes to improved hole injection system and hole transport properties. In the example where the composite is used for the first layer 103, the first layer 103 can also achieve ohmic contact with the first electrode 102; therefore, the selection of the first electrode material can be independent of the work function.

An oxide of a transition metal is preferably used as the inorganic compound for the composite material. Moreover, oxides of metals belonging to Groups 4 to 8 in the periodic table can be used. In particular, it is preferred to use vanadium oxide, cerium oxide, cerium oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide and cerium oxide because of their high electron accepting properties. Among them, molybdenum oxide is particularly preferred because it is stable under air, has low hygroscopic properties and is easy to handle.

It should be noted that this particular embodiment mode can be combined with any other specific embodiment mode as appropriate.

(Specific embodiment mode 7)

A light-emitting element in which a plurality of light-emitting units according to the present invention are stacked (hereinafter referred to as a stacked-type element) is described in this embodiment mode with reference to FIG. The light-emitting element is a stacked light-emitting element having a plurality of light-emitting units interposed between the first electrode and the second electrode. Structures similar to those described in the specific embodiment modes 3 to 6 are used in each of the light-emitting units. In other words, the light-emitting element described in the specific embodiment mode 3 It is a light-emitting element having one light-emitting unit. A light-emitting element having a plurality of light-emitting units is described in this embodiment mode.

In FIG. 3, the first light emitting unit 511 and the second light emitting unit 512 are stacked between the first electrode 501 and the second electrode 502. An electrode similar to that described in the embodiment mode 2 can be applied to the first electrode 501 and the second electrode 502. The first light emitting unit 511 and the second light emitting unit 512 may have the same structure or different structures, and may be applied similarly to the structures described in the specific embodiment modes 3 to 6.

The charge generating layer 513 includes a composite material of an organic compound and a metal oxide. The composite of the organic compound and the metal oxide is described in the specific embodiment mode 2 or 5, and includes an organic compound and a metal oxide such as vanadium oxide, molybdenum oxide or tungsten oxide. Various compounds can be used as the organic compound such as an aromatic amine compound, a carbazole derivative, an aromatic hydrocarbon, and a polymer compound such as an oligomer, a dendrimer or a polymer. The organic compound having a hole mobility of greater than or equal to 10 ^-6 cm 2 /volt second is preferably applied as an organic compound having hole transport properties. However, other substances than the compounds may be used as long as their hole transport properties are greater than their electron transport properties. The composite of organic compound and metal oxide has excellent carrier injection properties and carrier transport properties, and thus can achieve low voltage driving and low current driving.

It should be noted that the charge generating layer 513 can be formed by a combination of a composite of an organic compound and a metal oxide with other substances. For example, the charge generating layer 513 may contain a layer of a composite material of an organic compound and a metal oxide and a compound containing one selected from an electron-donating substance and have high electron transport properties. A combination of layers of the compound is formed. Further, the charge generating layer 513 may be formed by a combination of a layer of a composite material of an organic compound and a metal oxide and a transparent conductive film.

In any example, the charge generating layer 513 interposed between the first light emitting unit 511 and the second light emitting unit 512 is acceptable as long as the voltage is applied to the first electrode 501 and the second electrode 502. In the meantime, electrons are injected into one light-emitting unit and holes are injected into other light-emitting units. For example, in the example where the voltage is applied such that the potential of the first electrode is higher than the potential of the second electrode, the charge generating layer 513 of any structure is acceptable as long as the layer 513 injects electrons and holes to the first one, respectively. The light emitting unit 511 and the second light emitting unit 512 may be used.

A light-emitting element having two kinds of light-emitting units is described in this embodiment mode; however, the present invention is applicable to a light-emitting element in which three or more light-emitting units are stacked. By arranging a plurality of light-emitting units between a pair of electrodes, a plurality of light-emitting units are separated by a charge generating layer, and the light-emitting element of this embodiment mode can maintain a low current density to achieve a high light-emitting area. Long-life components. In the case where the light-emitting element is applied to an illumination system, since the voltage drop against the electrode material can be lowered; therefore, uniform light emission over a large area is possible. Furthermore, low voltage driving is possible, and a light emitting device with low power consumption can be realized.

This particular embodiment mode can be combined with any other specific embodiment mode as appropriate.

(Specific embodiment mode 8)

A light-emitting device manufactured using the anthracene derivative of the present invention is described in this specific embodiment mode.

A light-emitting device manufactured using the anthracene derivative of the present invention is described in this embodiment mode with reference to Figs. 4A and 4B. 4A is a top view showing the light-emitting device and FIG. 4B is a cross-sectional view of FIG. 4A taken along lines A-A' and B-B'. The drive circuit portion (source drive circuit), the pixel portion, and the drive circuit portion (gate drive circuit) are represented by reference numerals 601, 602, and 603, respectively, and are indicated by broken lines. The sealing substrate and the sealing material are also represented by reference numerals 604 and 605, respectively, and the portion surrounded by the sealing material 605 corresponds to the space 607.

The guiding line 608 is a line for transmitting the input signal to the source driving circuit 601 and the gate driving circuit 603, and the line 608 receives the video signal, the clock signal, the start signal, the reset signal, and the FPC from the external input terminal (soft printing) Circuit board) 609 similar signal. It should be noted that only the FPC is shown here; however, the FPC is provided with a printed circuit board (PWB). The light-emitting device in the specification of the present invention includes not only the light-emitting device itself but also a light-emitting device connected to the FPC or PWB.

Next, the cross-sectional structure is described with reference to FIG. 4B. The driver circuit portion and the pixel portion are formed on the element substrate 610. The source drive circuit 601 (which is the drive circuit portion) and one pixel in the pixel portion 602 are shown here.

A CMOS circuit, which is a combination of the n-channel TFT 623 and the p-channel TFT 624, is formed as a source driving circuit 601. The drive circuit can be formed using various CMOS circuits, PMOS circuits, or NMOS circuits. Although The drive integrated type device in which the drive circuit is formed on the substrate is described in this embodiment mode, but the drive circuit is not necessarily formed on the substrate but may be formed outside the substrate.

The pixel portion 602 has a plurality of pixels, and each of the pixels includes a switching TFT 611, a current controlling TFT 612, and a first electrode 613 electrically connected to the current controlling TFT 612 tube. It should be noted that the formed insulator 614 covers the end portion of the first electrode 613. Here, a positive type photosensitive acryl film is used for the insulator 614.

The formed insulator 614 is formed into a curved surface having a curvature at its upper end portion or lower end portion in order to obtain favorable coverage. For example, in the case of using a positive type photosensitive acrylic resin as a material for the insulator 614, it is preferable to form an insulator 614 having a curved surface having a radius of curvature (0.2 μm to 3 μm) only at the upper end portion. A negative type resin which is insoluble in an etchant by light irradiation or a positive type resin which is dissolved in an etchant by light irradiation can be used for the insulator 614.

The EL layer 616 and the second electrode 617 are formed on the first electrode 613. Here, a material having a work function is preferably used as a material of the first electrode 613 serving as an anode. For example, the first electrode 613 can be formed by using a titanium nitride film and a stacked layer of a film containing aluminum as its main component; a titanium nitride film, a film containing aluminum as its main component, and a titanium nitride film. Layer structure; or the like, and a single layer film, such as an ITO film, an indium tin oxide film containing antimony, an indium oxide film containing 2 to 20% by weight of zinc oxide, a titanium nitride film, a chromium film, a tungsten film, Zn Formed by a film or a Pt film. When the first electrode 613 has a stacked structure, the electrode 613 exhibits a low resistance enough to function as a line. To a favorable ohmic contact.

Further, the EL layer 616 is formed by various methods such as an evaporation method using a vapor hood, an inkjet method, and a spin coating method. The EL layer 616 includes the anthracene derivative of the present invention described in the embodiment mode 2. Further, the EL layer 616 can be formed using another material containing a low molecular compound or a high molecular compound (containing an oligomer and a dendrimer).

It is preferable to use a material having a low work function (Al, Mg, Li, Ca, or an alloy thereof or a compound such as MgAg, MgIn, AlLi, LiF or CaF ₂ ) as being formed on the EL layer 616 and serving as a cathode. The material of the second electrode 617. In the example in which the light generated in the EL layer 616 is transmitted via the second electrode 617, a metal thin film and a transparent conductive film (ITO, indium oxide containing 2 to 20% by weight of zinc oxide, containing A stacked layer of indium oxide-tin oxide, zinc oxide (ZnO) or the like of cerium oxide or cerium oxide is used as the second electrode 617.

By connecting the sealing substrate 604 and the element substrate 610 with the sealing material 605, the light-emitting elements 618 of the present invention shown in the specific embodiment modes 3 to 7 are used for the element substrate 610, the sealing substrate 604, and the sealing material 605. Surrounded by space 607. It should be noted that an inert gas (nitrogen, argon or the like) fills the space 607. There is also an example in which the space 607 is filled with the sealing material 605.

It should be noted that an epoxy resin-based resin is preferably used as the sealing material 605. It is expected that the material will allow as little moisture and oxygen penetration as possible. A plastic substrate and glass formed of FRP (fiber glass reinforced plastic), PVF (polyvinyl fluoride), polyester, acrylic resin or the like can be used. A substrate or a quartz substrate is used as the sealing substrate 604.

As described above, a light-emitting device containing the anthracene derivative of the present invention can be obtained.

Since the anthracene derivative described in the specific embodiment mode 2 is used for the light-emitting device of the present invention, a light-emitting device having high performance can be obtained. In particular, a light-emitting device having a long life can be obtained.

Also, since the anthracene derivative of the present invention has high luminous efficiency, a light-emitting device having low power consumption can be obtained.

Furthermore, since the anthracene derivative of the present invention is capable of emitting blue light having high color purity, the anthracene derivative can be advantageously used for a full color display. Furthermore, since the anthracene derivative of the present invention can emit blue light having high reliability and low power consumption, it can be advantageously used for a full color display.

Further, the anthracene derivative of the present invention can emit blue light having high color purity, so that a light-emitting device having high color reproducibility can be obtained.

As described above, an active matrix light-emitting device that controls a light-emitting element having a transistor is described in this embodiment mode; however, a passive matrix light-emitting device can be used. A perspective view of a passive matrix illumination device fabricated using the present invention is shown in Figure 5A. 5A is a perspective view of the light emitting device and FIG. 5B is a cross-sectional view of FIG. 5A taken along line X-Y. In FIGS. 5A and 5B, an EL layer 955 is used on the substrate 951 between the electrode 952 and the electrode 956. The end of the electrode 952 is covered with an insulating layer 953. A spacer layer 954 is then used on the insulating layer 953. The side walls of the spacer layer 954 are inclined such that the distance between one side wall and the other side walls is narrowed toward the surface of the substrate. In other words, the cross section of the spacer layer 954 in the short side direction It is trapezoidal, and the bottom (the side extending in the direction similar to the planar direction of the insulating layer 953 and in contact with the insulating layer 953) is longer than the upper side (in the direction similar to the planar direction of the insulating layer 953 and not with the insulating layer 953) The side of the contact) is shorter. The spacer layer 954 provided in this manner can avoid defects of the light-emitting element due to static electricity. In the example of the passive matrix light-emitting device, a light-emitting device having high reliability and long life can also be obtained by using the anthracene derivative of the present invention. Furthermore, a light-emitting device with low power consumption can be obtained.

(Specific embodiment mode 9)

The electronic device of the present invention partially containing the light-emitting device described in Embodiment Mode 8 is described in this embodiment mode. The electronic device of the present invention comprises the anthracene derivative described in Embodiment Mode 2, and has a display portion of high reliability and long life. The electronic device of the present invention also has a display portion with low power consumption.

Providing cameras such as video cameras or digital cameras, glasses-type displays, navigation systems, audio-visual reproduction devices (automotive stereo combinations, stereo combinations or the like), computers, game consoles, portable information terminals (handheld computers, Mobile phone, portable game console, e-book or the like) and an image reproduction device for recording media (especially a device capable of re-displaying a recording medium such as a digital versatile disc (DVD), and all of which can display images. An apparatus for a display device and the like as an electronic device including a light-emitting element manufactured using the anthracene derivative of the present invention. Specific examples of such electronic devices are shown in Figures 6A through 6D.

6A shows a television device according to the present invention including a frame 9101, a support base 9102, a display portion 9103, a horn portion 9104, a video input terminal 9105, and the like. In the television device, the display portion 9103 has light-emitting elements similar to those described in the specific embodiment modes 3 to 7, and the light-emitting elements are arranged in a matrix. The characteristics of the light-emitting element are exemplified by high luminous efficiency and long life. The display portion 9103 containing the light-emitting elements has similar features. Therefore, in the television device, the image quality is never deteriorated and low power consumption is achieved. Due to these characteristics, the deterioration compensation function and the power supply circuit can be significantly reduced or the size in the television device can be reduced, which can reduce the size and weight of the frame 9101 and the support base 9102. In the television device according to the present invention, low power consumption, high image quality, and small size and light weight are achieved; therefore, a product suitable for a living environment can be provided. Also, since the anthracene derivative described in the embodiment mode 1 can have a blue light of high color purity, a full color display is possible, and a television device having a display portion with high color reproducibility can be obtained. Furthermore, a television device having a display portion having a long life can be obtained.

6B shows a computer according to the present invention including a main body 9201, a frame 9202, a display portion 9203, a keyboard 9204, an external connection port 9205, a pointing device 9206, and the like. In the computer, the display portion 9203 has light-emitting elements similar to those described in the specific embodiment modes 3 to 7, and the light-emitting elements are arranged in a matrix. The characteristics of the light-emitting element are exemplified by high luminous efficiency and long life. The display portion 9203 containing the light-emitting elements has similar features. Therefore, in a computer, image quality never deteriorates and lower power consumption is achieved. Due to these characteristics, the deterioration compensation function and The power supply circuit significantly reduces or reduces the size in the computer; therefore, the small size and light weight of the main body 9201 and the frame 9202 can be achieved. In the computer according to the present invention, low power consumption, high image quality, and small size and light weight are achieved; therefore, products suitable for the environment can be supplied. Further, since the anthracene derivative described in Embodiment Mode 1 can have a blue light of high color purity, a full color display is possible, and a computer having a display portion with high color reproducibility can be obtained. Furthermore, a computer having a long-life display portion can be obtained.

6C shows a mobile phone according to the present invention, which includes a main body 9401, a frame 9402, a display portion 9403, a video input portion 9404, a video output portion 9405, operation keys 9406, an external connection port 9407, an antenna 9408, and the like. In the mobile phone, the display portion 9403 has light-emitting elements similar to those described in the specific embodiment modes 3 to 7, and the light-emitting elements are arranged in a matrix. The characteristics of the light-emitting element are exemplified by high luminous efficiency and long life. The display portion 9403 containing the light-emitting elements has similar features. Therefore, in mobile phones, image quality never deteriorates and lower power consumption is achieved. Due to these characteristics, the deterioration compensation function and the power supply circuit can be remarkably reduced or the size in the mobile phone can be reduced; therefore, the small size and light weight of the main body 9401 and the frame 9402 can be achieved. In the mobile phone according to the present invention, low power consumption, high image quality, and small size and light weight are achieved; therefore, a product suitable for carrying can be provided. Further, since the anthracene derivative described in Embodiment Mode 1 can have a blue light of high color purity, a full color display is possible, and a mobile phone having a display portion with high color reproducibility can be obtained. again A mobile phone having a long-life display portion can be obtained.

6D shows a camera according to the present invention, which includes a main body 9501, a display portion 9502, a frame 9503, an external connection port 9504, a remote control receiving portion 9505, an image receiving portion 9506, a battery 9507, a video input portion 9508, an operation key 9509, Eyepiece portion 9510 and the like. In the camera, the display portion 9502 has light-emitting elements similar to those described in the specific embodiment modes 3 to 7, and the light-emitting elements are arranged in a matrix. The characteristics of the light-emitting element are exemplified by high luminous efficiency and long life. The display portion 9502 containing the light-emitting elements has similar features. Therefore, in the camera, the image quality is never deteriorated and a lower power consumption can be achieved. Due to these characteristics, the deterioration compensation function and the power supply circuit can be remarkably reduced or the size in the camera can be reduced; therefore, the small size and light weight of the main body 9501 can be achieved. In the camera according to the present invention, low power consumption, high image quality, and small size and light weight are achieved; therefore, a product suitable for carrying can be provided. Further, since the anthracene derivative described in the embodiment mode 1 can have a blue light of high color purity, a full color display is possible, and a camera having a display portion with high color reproducibility can be obtained. Furthermore, a camera having a long-life display portion can be obtained.

As described above, the applicable range of the light-emitting device of the present invention is so wide that the light-emitting device can be applied to electronic devices in various fields. An electronic device having a long-life display portion can be provided by using the anthracene derivative of the present invention. Furthermore, an electronic device having a display portion with high color reproducibility can be obtained.

The illumination device of the present invention can also be used as an illumination system. Use of this The mode of the inventive light-emitting element as an illumination system is described with reference to FIG.

Fig. 7 shows a liquid crystal display device using the light-emitting device of the present invention as a backlight. The liquid crystal display device shown in FIG. 7 includes a frame 901, a liquid crystal layer 902, a backlight 903, and a frame 904, and the liquid crystal layer 902 is coupled to the driving IC 905. The light emitting device of the present invention is used for the backlight 903, and the current is supplied via the joint 906.

A backlight having reduced power consumption and high luminous efficiency can be obtained by using the light-emitting device of the present invention as a backlight of a liquid crystal display device. The light-emitting device of the present invention is an illumination system having planar illumination and can have a large area. Therefore, the backlight can have a large area, and a liquid crystal display device having a large area can be obtained. Further, the light-emitting device of the present invention has a thin shape and low power consumption; therefore, a display device having a thin shape and low power consumption can be achieved. Since the light-emitting device of the present invention has a long life, the liquid crystal display device using the light-emitting device of the present invention also has a long life.

Fig. 8 shows an example of a light-emitting device to which the present invention is applied. In Fig. 8, an example of application to a table lamp as an illumination system is illustrated. The table lamp shown in Fig. 8 includes a frame 2001 and a light source 2002, and the light-emitting device of the present invention is used as the light source 2002. The light-emitting device of the present invention has high luminous efficiency and has a long life; therefore, the table lamp also has high luminous efficiency and long life.

Fig. 9 shows an example of a light-emitting device to which the present invention is applied. FIG. 9 shows an example of application to the indoor lighting system 3001. Since the light-emitting device of the present invention also has a large area, the light-emitting device of the present invention can be used as an illumination system having a large light-emitting area. Furthermore, the light-emitting device of the present invention has a thin Shape and low power consumption; the light-emitting device of the present invention can be used as an illumination system having a thin shape and low power consumption. As described in FIG. 6A, the television device 3002 according to the present invention is placed in a room in which the light-emitting device to which the present invention is applied is used as the indoor lighting device 3001, and public broadcasting and movies can be viewed. In this example, since the two devices consume low power, the effective image can be viewed in a bright room without worrying about the electricity bill.

[Specific Example 1]

The synthesis of 9-[4-(N-carbazolyl)]phenyl-10-benzoquinone (abbreviation: CzPA) represented by the formula (11) is described in this specific example.

[Step 1] Synthesis of 9-bromo-10-benzoquinone (i) Synthesis of 9-benzoquinone

The synthetic scheme of 9-phenylhydrazine is shown in (B-1).

25.7 grams (100 millimoles) of 9-bromoindole, 12.8 grams (105 millimoles) of phenylboronic acid, 233 milligrams (1.0 millimoles) of palladium (II) acetate, and 913 milligrams (3.0 millimoles) of three ( The o-tolylphosphine was placed in a 500 ml three-necked flask and subjected to nitrogen substitution. Next, 100 ml of ethylene glycol dimethyl ether and 75 ml (190 mmol) of an aqueous sodium carbonate solution (2.0 mol/liter) were added thereto, and the reaction mixture was stirred at 90 ° C for 5 hours. After the reaction, the reaction mixture was subjected to suction filtration, and the precipitated solid was collected. The obtained solid was dissolved in toluene, and the resulting solution was subjected to suction filtration through Florisil, diatomaceous earth and then alumina. The filtrate was washed with water and saturated brine, and then the organic layer was dried over magnesium sulfate. The mixture was naturally filtered and the filtrate was condensed to afford 25.0 g of light brown solid, 98% yield, as the subject matter.

(ii) Synthesis of 9-bromo-10-benzoquinone

The synthetic scheme of 9-bromo-10-benzoquinone is shown in (B-2).

25.0 g (98.3 mmol) of 9-phenylhydrazine was placed in a 1 liter three-necked flask, and 300 ml of carbon tetrachloride was added thereto. A solution in which 15.6 g (98.3 mmol) of bromine was dissolved in 40 ml of carbon tetrachloride was dropped into the reaction solution at room temperature. After the completion of the dropwise addition, the reaction solution was stirred at room temperature for 1 hour. The reaction was then completed by the addition of aqueous sodium thiosulfate solution and the solution was stirred for an additional hour. The organic layer of the reaction mixture was washed with aqueous sodium hydroxide (2.0 m/l) and brine and dried over magnesium sulfate. The mixture was naturally filtered and the filtrate was condensed to give a solid. The solid was dissolved in toluene, and the resulting solution was subjected to suction filtration through magnesium ruthenate, diatomaceous earth and then alumina. The filtrate was concentrated to give a solid, and the solid was recrystallized from a mixture of methylene chloride and hexane, whereby 27.8 g of a pale yellow powdery solid having an 85% yield was obtained as the subject matter.

[Step 2] Synthesis of 4-(carbazol-9-yl)phenylboronic acid (i) Synthesis of N-(4-bromophenyl)carbazole

The synthetic scheme of N-(4-bromophenyl)carbazole is shown in (B-3).

Will be 56.3 grams (0.24 moles) 1,4-dibromobenzene, 31.3 grams (0.18 mol) carbazole, 4.6 g (0.024 mol) cuprous iodide (I), 66.3 g (0.48 mol) potassium carbonate and 2.1 g (0.008 mol) 18-coron-6-ether in 300 Dilute in a three-necked flask and replace with nitrogen. Next, 8 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) was added thereto, and the reaction mixture was stirred at 180 ° C for 6 hours. After the reaction mixture was cooled to room temperature, the precipitate was removed by suction filtration. The filtrate was washed in this order with diluted hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of brine. The organic layer was dried over magnesium sulfate. After drying, the mixture was naturally filtered and the filtrate was concentrated to give an oily material. The material was purified by silica gel column chromatography (hexane: ethyl acetate = 9:1). The obtained solid was recrystallized from a mixed solvent of chloroform and hexane, whereby 20.7 g of light brown thin plate crystals having a yield of 35% were obtained, which was the subject matter.

(ii) Synthesis of 4-(carbazol-9-yl)phenylboronic acid

The synthetic scheme of 4-(carbazol-9-yl)phenylboronic acid is shown in (B-4).

Place 21.8 grams (67.5 millimoles) of N-(4-bromophenyl)carbazole Into a 500 ml three-necked flask and replace with nitrogen. Then, 200 ml of tetrahydrofuran (THF) was added to maintain the inside of the reaction system at -78 °C. 48.9 ml (74.3 mmol) of n-butyllithium (1.52 mol/liter hexane solution) was dropped into the reaction solution, and the solution was stirred at the same temperature for 2 hours. 17.4 ml (155 mmol) of trimethyl borate was added and the solution was stirred at -78 °C for 1 hour, and then the solution was stirred for 12 hours while allowing the reaction temperature to gradually increase to room temperature. After the reaction, 200 ml of hydrochloric acid (1 mol/liter) was added to the reaction solution, and the solution was stirred at room temperature for 1 hour. The reaction mixture was washed with water and aq. The extracted solution was washed with a saturated brine and dried over magnesium sulfate. After drying, the mixture was subjected to suction filtration and the filtrate was condensed to obtain a solid. The solid was recrystallized from a mixed solution of chloroform and hexane, whereby 12.8 g of a white powdery solid having a yield of 66% was obtained as the subject matter.

[Step 3] Synthesis of 9-[4-(N-carbazolyl)]phenyl-10-benzoquinone (abbreviation: CzPA)

The synthetic scheme of CzPA is shown in (B-5).

1.44 g (4.32 mmol) of 9-bromo-10-benzoquinone, 1.49 g (5.19 mmol) of 4-(carbazol-9-yl)phenylboronic acid carbazole, 38.0 mg (0.17 mmol) Palladium(II) acetate and 0.36 g (1.21 mmol) of ginseng (o-tolyl)phosphine were placed in a 100 ml three-necked flask and subjected to nitrogen substitution. Next, 10 ml of ethylene glycol dimethyl ether (DME) and 6.5 ml (13.0 mmol) of an aqueous sodium carbonate solution (2.0 mol/liter) were added, and the solution was stirred at 90 ° C for 4 hours. The reaction mixture was then subjected to suction filtration and the precipitated solid was collected. The obtained solid was dissolved in chloroform, and the solution was subjected to suction filtration through magnesium ruthenate, diatomaceous earth and then alumina. The filtrate was condensed to obtain a solid, and the solid was recrystallized from a mixed solvent of chloroform and hexane, whereby 18.1 g of a pale yellow powdery solid having an 85% yield was obtained as a target. The compound was confirmed to be 9-[4-(N-carbazolyl)]phenyl-10-benzoquinone (abbreviation: CzPA) by nuclear magnetic resonance measurement (NMR).

The ¹ H NMR data of CzPA is shown below. ¹ H NMR (300 MHz, CDCl ₃ ); δ = 8.22 (d, J = 7.8 Hz, 2H), 7.86-7.82 (m, 3H), 7.61 - 7.36 (m, 20H). ^{The 1} H NMR chart is shown in Figures 10A and 10B. It should be noted that the range expansion of 6.5 ppm to 8.5 ppm in Fig. 10A is shown in Fig. 10B.

Thermogravimetric Analysis of CzPA - Differential Thermal Analysis (TG-DTA) was carried out using a thermogravimetric analyzer/differential thermal analyzer (TG/DTA 320, product of Seiko Instruments Inc.). The thermophysical properties were evaluated under nitrogen at a rate of temperature rise of 10 ° C / min. As a result, based on the relationship between gravity and temperature (measured by thermogravimetric analysis), the temperature under normal pressure was 348 ° C, which is the temperature under the gravity of the measurement starting point of gravity of 95% or less. The glass transition temperature and melting point of CzPA measured by a differential scanning calorimeter (Pyris 1 DSC, product of Perkin Elmer Co., Ltd.) were 125 ° C and 305 ° C, respectively; therefore, CzPA was found to be thermally stable.

Figure 11 shows the absorption spectrum of a toluene solution of CzPA. Figure 12 shows the absorption spectrum of a film of CzPA. An ultraviolet-visible spectrophotometer (V-550, manufactured by JASCO Corporation) was used for the measurement. The solution was placed in a quartz cell and the film sample was evaporated on a quartz substrate to form a sample. The absorption spectra from each of the reduced quartz absorption spectra are shown in Figures 11 and 12. In Figs. 11 and 12, the horizontal axis represents the wavelength (nano) and the vertical axis represents the absorption intensity (in units). In the case of the toluene solution, the absorption mainly based on the ruthenium skeleton was found to be about 376 nm and 396 nm, and in the case of the film, the absorption mainly based on the ruthenium skeleton was found at about 381 nm and 403 Nai. Meter. The emission spectrum (excitation wavelength: 370 nm) of the toluene solution of CzPA is shown in FIG. The emission spectrum (excitation wavelength: 390 nm) of the film of CzPA is shown in Fig. 14. In Figs. 13 and 14, the horizontal axis represents the wavelength (nano) and the vertical axis represents the luminous intensity. (in units). In the example of the toluene solution, the maximum emission wavelength is 448 nm (excitation wavelength: 370 nm), and in the example of the film, the maximum emission wavelength is 451 nm (excitation wavelength: 390 nm). It was found that blue light was obtained.

Further, the HOMO value of CzPA having a film state was -5.64 eV, which was measured in the air by a photoelectron spectrometer (AC-2, manufactured by Riken Keiki Co., Ltd.). Moreover, the absorption limit was obtained from the Tauc plot using data on the absorption spectrum of the film of CzPA in Fig. 12. When the absorption edge is evaluated as an optical energy gap, the energy gap is 2.95 eV. Therefore, the HOMO value is -2.69 eV.

Moreover, the oxidation-reduction reaction characteristics of CzPA are measured by cyclic voltammetry (CV) measurement. Further, an electrochemical analyzer (ALS type 600A, manufactured by BAS Inc.) was used for the measurement.

Dehydrated dimethylformamide (DMF, manufactured by Aldrich, 99.8%, catalog number: 22705-6) was used as the solvent for the solution used in the CV measurement. Tetra-n-butylammonium perchlorate (n-Bu ₄ NClO ₄ , manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) is a supporting electrolyte, which is dissolved in a solvent to make perchloric acid The concentration of n-butylammonium is 100 millimoles per liter. Moreover, the object to be measured was dissolved so that its concentration was set to 1 millimol/liter. Further, a platinum electrode (PTE platinum electrode, manufactured by BAS Inc.) was used as the working electrode. A platinum electrode (VC-3 Pt auxiliary electrode (5 cm), manufactured by BAS Inc.) was used as the auxiliary electrode. An Ag/Ag ⁺ electrode (RE5 non-aqueous solvent reference electrode, manufactured by BAS Inc.) was used as a reference electrode. This measurement was carried out at room temperature. It should be noted that the scanning speed of the CV measurement method was set to 0.1 volt/sec, and 100 cycles of scanning were performed for each of the oxidation end and the reduction end.

Figure 56 shows the results of CV measurement at the reducing end of CzPA and Figure 57 shows the results of CV measurement at the oxidized end of CzPA. In Figs. 56 and 57, the horizontal axis represents the potential (volts) of the working electrode with respect to the reference electrode, and the vertical axis represents the current flow value (microamperes) between the working electrode and the auxiliary electrode.

In the CzPA example, the reversible peaks from Figures 56 and 57 are shown at the oxidized and reduced ends. In addition, the peak intensity is not easily changed even when the oxidation is repeated 100 times to reduction or reduction to the oxidation cycle. From the above, it has been found that the anthracene derivative of the present invention is very stable to repeated oxidation-reduction reactions.

[Specific Example 2]

The synthesis method of 9-(biphenyl-4-yl)-10-[4-(carbazol-9-yl)phenyl]anthracene (abbreviation: PPCzPA) represented by the structural formula (12) is described in this embodiment. In the example.

[Step 1] Synthesis of 9-(4-biphenyl)-10-bromoindole (i) Synthesis of 9-(biphenyl-4-yl)indole

The synthetic scheme of 9-(biphenyl-4-yl)anthracene is shown in (C-1).

Put 5.1 g (20 mmol) of 9-bromoindole, 4.0 g (20 mmol) of 4-biphenylboronic acid and 246 mg (0.80 mmol) of tris(o-tolyl)phosphine into 100 ml of three In a neck flask, and carry out nitrogen substitution in the system. 20 ml of ethylene glycol dimethyl ether (DME) was added to the mixture, and the mixture was stirred and degassed under reduced pressure. Then add 45 mg (0.20 mmol) of palladium (II) acetate and 10 ml (2.0 m / liter) Potassium carbonate solution. The reaction mixture was stirred at 80 ° C for 3 hours under a stream of nitrogen. The reaction mixture was then cooled to room temperature, and the precipitated solid was collected by suction filtration. The collected solid was dissolved in toluene, and the solution was subjected to suction filtration through magnesium ruthenate, diatomaceous earth, and then alumina. The filtrate was condensed to give a solid, and the solid was recrystallized from ethanol, whereby 5.4 g of a white powdery solid having a yield of 81% was obtained as the subject matter.

(ii) Synthesis of 9-(biphenyl-4-)-10-bromoindole

The synthetic scheme of 9-(biphenyl-4-yl)-10-bromoindole is shown in (C-2).

5.3 g (16 mmol) of 9-(biphenyl-4-yl)indole and 90 ml of carbon tetrachloride were placed in a 200 ml three-necked flask and stirred. A solution in which 2.8 g (18 mmol) of bromine was dissolved in 10 ml of carbon tetrachloride was dropped into the above solution through a dropping funnel. The solution was then stirred at room temperature for 1 hour, and an aqueous sodium thiosulfate solution was added to the reaction solution to complete the reaction. The aqueous layer of the reaction mixture was extracted with chloroform, and the extracted solution was washed with the organic layer in saturated sodium hydrogen carbonate and saturated brine. The organic layer was dried over magnesium sulfate and the mixture was filtered naturally to remove Magnesium sulfate. The filtrate was then condensed to give a solid. The solid obtained was recrystallized from ethanol, whereby 5.4 g of a yellow powdery solid having a yield of 82% was obtained, which was the subject matter.

[Step 2] Synthesis of 9-(biphenyl-4-yl)-10-[4-(carbazol-9-yl)phenyl]anthracene (abbreviation: PPCzPA)

The synthetic scheme of PPCzPA is shown in (C-3).

3.0 g (7.3 mmol) of 9-(biphenyl-4-yl)-10-bromoindole and 2.1 g (7.3 mmol) of 4-(carbazol-9-yl)phenylboronic acid were placed in 100 ml. In a three-necked flask, nitrogen substitution in the system was carried out. 25 ml of ethylene glycol dimethyl ether (DME) and 10 ml (2.0 mol/liter) of potassium carbonate solution were added to the mixture, and the mixture was stirred and degassed under reduced pressure. Then 85 mg (0.017 mmol) of ruthenium (triphenylphosphine) palladium (0) was added. The reaction mixture was stirred at 80 ° C for 12 hours under a stream of nitrogen. The reaction mixture is then cooled to room temperature and the precipitated solid is pumped Gas filtration collection. The collected solid was dissolved in toluene, and the solution was subjected to suction filtration through magnesium ruthenate, diatomaceous earth, and then alumina. The filtrate was condensed to obtain a solid, and the solid was recrystallized from a mixed solvent of chloroform and hexane, whereby 2.9 g of a pale yellow powdery solid having a yield of 72% was obtained as a target. The compound was confirmed to be 9-(biphenyl-4-yl)-10-[4-(carbazol-9-yl)phenyl]anthracene (abbreviation: PPCzPA) by nuclear magnetic resonance measurement (NMR).

The ¹ H NMR data of PPCzPA is shown below. ¹ H NMR (300 MHz, CDCl ₃ ); δ = 7.33 - 7.61 (m, 13H), 7.68 - 7.88 (m, 14H), 8.21. (d, J = 7.8 Hz, 2H). ^{The 1} H NMR chart is shown in Figures 15A and 15B. It should be noted that the range expansion of 6.5 ppm to 8.5 ppm in Fig. 15A is shown in Fig. 15B.

When 2.18 g of PPCzPA obtained by the above synthesis method was purified by sublimation for 12 hours under the conditions of an argon gas flow of 3.0 ml/min, a pressure of 7.0 Pascal, and a heating temperature of 290 ° C, a yield of 74% was obtained. Light yellow needle-like crystals of 1.61 g of PPCzPA.

Thermogravimetric Analysis - Differential Thermal Analysis (TG-DTA) of PPCzPA was carried out using a thermogravimetric analyzer/differential thermal analyzer (TG/DTA 320, product of Seiko Instruments Inc.). As a result, based on the relationship between gravity and temperature (thermogravimetric analysis), the temperature under normal pressure was 390 ° C, which is the temperature under the gravity of the measurement starting point of gravity of 95% or less. PPCzPA was found to have beneficial heat resistance.

Figure 16 shows the absorption spectrum of a toluene solution of PPCzPA. Figure 17 shows the absorption spectrum of a film of PPCzPA. The measurement uses UV-visible light A spectrophotometer (V-550, manufactured by JASCO Corporation) was used. The solution was placed in a quartz bath and the film was evaporated on a quartz substrate to form a sample. The absorption spectra from each of the reduced quartz absorption spectra are shown in Figures 16 and 17. In Figs. 16 and 17, the horizontal axis represents the wavelength (nano) and the vertical axis represents the absorption intensity (in units). In the case of the toluene solution, the absorption mainly based on the ruthenium skeleton was found to be about 376 nm and 398 nm, and in the case of the film, the absorption mainly based on the ruthenium skeleton was found at about 382 nm and 404 Nai. Meter. The luminescence spectrum (excitation wavelength: 370 nm) of the toluene solution of PPCzPA is shown in Fig. 18, and the luminescence spectrum (excitation wavelength: 380 nm) of the film of PPCzPA is shown in Fig. 19. In Figs. 18 and 19, the horizontal axis represents the wavelength (nano) and the vertical axis represents the luminous intensity (in units of cells). In the example of the toluene solution, the maximum emission wavelength was 429 nm (excitation wavelength: 370 nm), and in the example of the film, it was 450 nm (excitation wavelength: 380 nm).

Further, the HOMO value of PPCzPA having a film state was -5.59 eV, which was measured in the air by a photoelectron spectrometer (AC-2, manufactured by Riken Keiki Co., Ltd.). Moreover, the absorption limit was obtained from the Tauc plot using data on the absorption spectrum of the film of PPCzPA in Fig. 17. When the absorption limit is evaluated as an optical energy gap, the energy gap is 2.92 eV. Therefore, the HOMO value is -2.67 eV.

Moreover, the oxidation-reduction reaction characteristics of PPCzPA were measured by cyclic voltammetry (CV) measurement. Further, an electrochemical analyzer (ALS type 600A, manufactured by BAS Inc.) was used for the measurement.

Dehydrated dimethylformamide (DMF, manufactured by Aldrich, 99.8%, catalog number: 22705-6) was used as the solvent for the solution used in the CV measurement. Tetra-n-butylammonium perchlorate (n-Bu ₄ NClO ₄ , manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) is a supporting electrolyte, which is dissolved in a solvent to make perchloric acid The concentration of n-butylammonium is 100 millimoles per liter. Moreover, the object to be measured was dissolved so that its concentration was set to 1 millimol/liter. Further, a platinum electrode (PTE platinum electrode, manufactured by BAS Inc.) was used as the working electrode. A platinum electrode (VC-3 Pt auxiliary electrode (5 cm), manufactured by BAS Inc.) was used as the auxiliary electrode. An Ag/Ag ⁺ electrode (RE5 non-aqueous solvent reference electrode, manufactured by BAS Inc.) was used as a reference electrode. It should be noted that this measurement is carried out at room temperature.

The reduction reaction characteristics of PPCzPA were measured as follows. After the potential was changed from -0.47 volts to -2.50 volts, the scan of the potential of the working electrode with respect to the reference electrode was changed from -2.50 volts to -0.47 volts, and was set to one cycle, and 100 cycles were measured. Further, the oxidation reaction characteristics of PPCzPA were measured as follows. After the potential was changed from -0.33 volts to 1.30 volts, the scan with respect to the potential of the working electrode of the reference electrode changed from 1.30 volts to -0.33 volts was set to one cycle, and 100 cycles were measured. Furthermore, the scanning speed of the CV measurement method was set to 0.1 volt/sec.

Figure 58 shows the results of CV measurement at the reducing end of PPCzPA and Figure 59 shows the results of CV measurement at the oxidized end of PPCzPA. In Figs. 58 and 59, the horizontal axis shows the potential (volts) of the working electrode with respect to the reference electrode, and the vertical axis shows the current flow value (microamperes) between the working electrode and the auxiliary electrode.

In the example of PPCzPA, the reversible peaks from Figures 58 and 59 are shown at the oxidized and reduced ends. In addition, the peak intensity is not easily changed even when the oxidation is repeated 100 times to reduction or reduction to the oxidation cycle. From the above, it has been found that the anthracene derivative of the present invention is very stable to repeated oxidation-reduction reactions.

[Specific Example 3]

The synthesis method of 9-(4-t-butylphenyl)-10-[4-(carbazol-9-yl)]benzoquinone (abbreviation: PTBCzPA) represented by the structural formula (20) is described in this embodiment. In the example.

[Step 1] Synthesis of 9-bromo-10-(4-tert-butylphenyl)fluorene (i) Synthesis of 9-(4-t-butylphenyl)anthracene

The synthetic scheme of 9-(4-t-butylphenyl)anthracene is shown in (D-1).

Put 5.1 grams (20 millimoles) of 9-bromoindole, 3.6 grams (20 millimoles) of 4-tert-butylphenylboronic acid and 244 milligrams (0.80 millimoles) of tris(o-tolyl)phosphine into 100 Dilute in a three-necked flask and carry out nitrogen substitution in the system. 20 ml of ethylene glycol dimethyl ether (DME) was added to the mixture, and the mixture was stirred and degassed under reduced pressure. Then 45 mg (0.20 mmol) of palladium (II) acetate and 10 ml (2.0 mol/L) potassium carbonate solution were added. The reaction mixture was stirred at 80 ° C for 3 hours under a stream of nitrogen. The reaction mixture was then cooled to room temperature, and the precipitated solid was collected by suction filtration. The collected solid was dissolved in toluene, and the solution was subjected to suction filtration through magnesium ruthenate, diatomaceous earth, and then alumina. The filtrate was condensed to give a solid, and the solid was recrystallized from ethanol, whereby 5.0 g of a white powdery solid having a yield of 81% was obtained as the subject matter.

(ii) Synthesis of 9-bromo-10-(3-tert-butylphenyl)fluorene

The synthetic scheme of 9-bromo-10-(4-tert-butylphenyl)fluorene is shown in (D-2).

5.0 g (16.0 mmol) of 9-(4-t-butylphenyl) hydrazine and 90 ml of carbon tetrachloride were placed in a 500 ml three-necked flask and stirred. A solution in which 2.8 g (18 mmol) of bromine was dissolved in 10 ml of carbon tetrachloride was dropped into the above solution through a dropping funnel. The solution was then stirred at room temperature for 1 hour, and an aqueous sodium thiosulfate solution was added to the reaction solution to complete the reaction. The aqueous layer of the reaction mixture was extracted with chloroform, and the extracted solution was washed with a saturated aqueous sodium hydrogen carbonate solution and brine. The organic layer was dried over magnesium sulfate and the mixture was filtered thoroughly to remove magnesium sulfate. The filtrate was then condensed to give a solid. The obtained solid was recrystallized from ethanol, whereby 6.3 g of a yellow powdery solid having a yield of 99% was obtained, which was the subject matter.

[Step 2] Synthesis of 9-(4-t-butylphenyl)-10-[4-(carbazol-9-yl)]benzoquinone (abbreviation: PTBCzPA)

The synthetic scheme of PTBCzPA is shown in (D-3).

Put 2.0 g (5.1 mol) of 9-bromo-10-(4-tert-butylphenyl)fluorene and 1.5 g (5.1 mmol) of 4-(carbazol-9-yl)phenylboronic acid into 100 Dilute in a three-necked flask and carry out nitrogen substitution in the system. 25 ml of ethylene glycol dimethyl ether (DME) and 10 ml (2.0 mol/liter) of potassium carbonate solution were added to the mixture, and the mixture was stirred and degassed under reduced pressure. Then 85 mg (0.017 mmol) of ruthenium (triphenylphosphine) palladium (0) was added. The reaction mixture was stirred at 80 ° C for 12 hours under a stream of nitrogen. The reaction mixture was then cooled to room temperature, and the precipitated solid was collected by suction filtration. The collected solid was dissolved in toluene, and the solution was subjected to suction filtration through magnesium ruthenate, diatomaceous earth, and then alumina. The filtrate was condensed to give a solid, which was purified by silica gel column chromatography (hexane: toluene = 7:3). The obtained solid was recrystallized from hexane, whereby 912 mg of pale yellow powdery crystals having a yield of 32% was obtained as the subject matter. The compound was confirmed to be 9-(4-t-butylphenyl)-10-[4-(carbazol-9-yl)]benzoquinone by nuclear magnetic resonance measurement (NMR) (abbreviation: PTBCzPA).

The ¹ H NMR data of PTBCzPA is shown below. ¹ H NMR (300 MHz, CDCl ₃ ); δ = 1.50 (s, 9H), 7.33 - 7.54 (m, 10H), 7.62 - 7.85 (m, 12H), 8.21. (d, J = 7.8 Hz, 2H). ^{The 1} H NMR chart is shown in Figures 20A and 20B. It should be noted that the range expansion of 6.5 ppm to 8.5 ppm in Fig. 20A is shown in Fig. 20B.

When 901 mg of PTBCzPA obtained by the above synthesis method was purified by sublimation for 12 hours under the conditions of an argon gas flow of 20.0 ml/min, a pressure of 200 Pascal, and a heating temperature of 300 ° C, a yield of 93% was obtained. Light yellow needle-like crystals of 839 mg PTBCzPA.

Thermogravimetric Analysis - Differential Thermal Analysis (TG-DTA) of PTBCzPA was carried out using a thermogravimetric analyzer/differential thermal analyzer (TG/DTA 320, product of Seiko Instruments Inc.). As a result, based on the relationship between gravity and temperature (thermogravimetric analysis), the temperature under normal pressure was 377 ° C, which is the temperature under the gravity of the measurement starting point of gravity of 95% or less. PTBCzPA was found to have beneficial heat resistance.

Figure 21 shows the absorption spectrum of a toluene solution of PTBCzPA. Figure 22 shows the absorption spectrum of the film of PTBCzPA. This measurement was carried out using a UV-visible spectrophotometer (V-550, manufactured by JASCO Corporation). The solution was placed in a quartz bath and the film was evaporated on a quartz substrate to form a sample. The absorption spectra from each of the reduced quartz absorption spectra are shown in Figures 21 and 22. In Figs. 21 and 22, the horizontal axis represents the wavelength (nano) and the vertical axis represents the absorption intensity (in units). In the case of a toluene solution, the absorption based on the ruthenium skeleton was found at about 376 nm. And 396 nm, and in the case of the film, the absorption based on the ruthenium skeleton was found at about 380 nm and 402 nm. The luminescence spectrum (excitation wavelength: 370 nm) of the toluene solution of PTBCzPA is shown in Fig. 23, and the luminescence spectrum (excitation wavelength: 380 nm) of the film of PTBCzPA is shown in Fig. 24. In Figs. 23 and 24, the horizontal axis represents the wavelength (nano) and the vertical axis represents the luminous intensity (in units). In the example of the toluene solution, the maximum emission wavelength was 423 nm (excitation wavelength: 370 nm), and in the example of the film, it was 443 nm (excitation wavelength: 380 nm).

Further, the HOMO value of the PTBCzPA having a film state was -5.72 eV, which was measured in the air by a photoelectron spectrometer (AC-2, manufactured by Riken Keiki Co., Ltd.). Moreover, the absorption limit was obtained from the Tauc plot using data on the absorption spectrum of the film of PTBCzPA in Fig. 22. When the absorption limit is evaluated as an optical energy gap, the energy gap is 2.95 eV. Therefore, the HOMO value is -2.77 eV.

Moreover, the oxidation-reduction reaction characteristics of PTBCzPA were measured by cyclic voltammetry (CV) measurement. Further, an electrochemical analyzer (ALS type 600A, manufactured by BAS Inc.) was used for the measurement.

Dehydrated dimethylformamide (DMF, manufactured by Aldrich, 99.8%, catalog number: 22705-6) was used as the solvent for the solution used in the CV measurement. Tetra-n-butylammonium perchlorate (n-Bu ₄ NClO ₄ , manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) is a supporting electrolyte, which is dissolved in a solvent to make perchloric acid The concentration of n-butylammonium is 100 millimoles per liter. Moreover, the object to be measured was dissolved so that its concentration was set to 1 millimol/liter. Further, a platinum electrode (PTE platinum electrode, manufactured by BAS Inc.) was used as the working electrode. A platinum electrode (VC-3 Pt auxiliary electrode (5 cm), manufactured by BAS Inc.) was used as the auxiliary electrode. An Ag/Ag ⁺ electrode (RE5 non-aqueous solvent reference electrode, manufactured by BAS Inc.) was used as a reference electrode. It should be noted that this measurement is carried out at room temperature.

The reduction reaction characteristics of PTBCzPA were measured as follows. After the potential was changed from -0.25 volts to -2.40 volts, the scan of the potential of the working electrode with respect to the reference electrode was changed from -2.40 volts to -0.25 volts, and was set to one cycle, and 100 cycles were measured. Further, the oxidation reaction characteristics of PTBCzPA were measured as follows. After the potential was changed from -0.33 volts to 1.30 volts, the scan with respect to the potential of the working electrode of the reference electrode changed from 1.30 volts to -0.33 volts was set to one cycle, and 100 cycles were measured. Furthermore, the scanning speed of the CV measurement method was set to 0.1 volt/sec.

Figure 60 shows the results of CV measurement at the reducing end of PTBCzPA and Figure 61 shows the results of CV measurement at the oxidized end of PTBCzPA. In Figs. 60 and 61, the horizontal axis shows the potential (volts) of the working electrode with respect to the reference electrode, and the vertical axis shows the current flow value (microamperes) between the working electrode and the auxiliary electrode.

In the example of PTBCzPA, the reversible peaks from Figures 60 and 61 are shown at the oxidized and reduced ends. In addition, the peak intensity is not easily changed even when the oxidation is repeated 100 times to reduction or reduction to the oxidation cycle. From the above, it has been found that the anthracene derivative of the present invention is very stable to repeated oxidation-reduction reactions.

[Specific Example 4]

The synthesis of 9-[4-(carbazol-9-yl)phenyl]-10-(4-trifluoromethylphenyl)anthracene (abbreviation: CF3CzPA) represented by the formula (42) is described herein. In a specific embodiment.

[Step 1] Synthesis of 9-bromo-10-(4-trifluoromethylphenyl)fluorene (i) Synthesis of 4-trifluoromethylphenylboronic acid

The synthetic scheme of 4-trifluoromethylphenylboronic acid is shown in (E-1).

33 g (0.15 mol) of 4-bromotrifluoromethylbenzene was placed in a 500 ml three-necked flask and subjected to nitrogen substitution in the system. Next, 200 ml of tetrahydrofuran (THF) was added thereto, and the mixture was stirred. Will The mixture solution was stirred at -78 ° C, and 100 ml (0.16 mol) of n-butyllithium (1.6 mol/liter) was dropped into the solution via a dropping funnel. The obtained solution was then stirred at the same temperature for 1 hour, and 22.3 ml (0.20 mol) of trimethyl borate was added and stirred for about 12 hours while allowing the reaction temperature to gradually increase to room temperature. Next, 100 ml of diluted hydrochloric acid (1 mol/liter) was added to the reaction solution, and the solution was stirred for 1 hour. The aqueous layer of the mixture was extracted three times with ethyl acetate. The mixture was naturally filtered to remove magnesium sulfate, and the filtrate was condensed to give a solid. The solid was washed with chloroform to give 15 g of a white solid, 54% yield, as the subject matter.

(ii) Synthesis of 9-(4-trifluoromethylphenyl)indole

The synthetic scheme of 9-(4-trifluoromethylphenyl)fluorene is shown in (E-2).

Put 5.1 grams (20 millimoles) of 9-bromoindole, 3.8 grams (20 millimoles) of 4-trifluoromethylphenylboronic acid and 244 mg (0.80 millimoles) of tris(o-tolyl)phosphine A 100 ml three-necked flask was placed and subjected to nitrogen substitution in the system. Add 20 ml of ethylene glycol dimethyl ether (DME) to the The mixture was stirred and degassed under reduced pressure. Then 45 mg (0.20 mmol) of palladium (II) acetate and 10 ml (2.0 mol/L) potassium carbonate solution were added. The reaction mixture was stirred at 80 ° C for 3 hours under a stream of nitrogen. The reaction mixture was then cooled to room temperature, and the precipitated solid was collected by suction filtration. The collected solid was dissolved in toluene, and the solution was subjected to suction filtration through magnesium ruthenate, diatomaceous earth, and then alumina. The filtrate was condensed to give a solid, and the solid was recrystallized from ethanol, whereby 5.7 g of a white powdery solid having a yield of 88% was obtained as the subject matter.

(iii) Synthesis of 9-bromo-10-(4-trifluoromethylphenyl)indole

The synthetic scheme of 9-bromo-10-(4-trifluoromethylphenyl)fluorene is shown in (E-3).

5.7 g (18 mmol) of 9-(4-trifluoromethylphenyl)phosphonium and 90 ml of carbon tetrachloride were placed in a 500 ml three-necked flask and stirred. A solution in which 3.2 g (20 mmol) of bromine was dissolved in 10 ml of carbon tetrachloride was dropped into the above solution through a dropping funnel. The solution was then stirred at room temperature for 1 hour, and an aqueous sodium thiosulfate solution was added to the reaction solution to complete the reaction. The aqueous layer of the reaction mixture was extracted with chloroform and extracted. The solution was washed with a saturated solution of sodium hydrogencarbonate and saturated brine with an organic layer. The organic layer was dried over magnesium sulfate and the mixture was filtered thoroughly to remove magnesium sulfate. The filtrate was then condensed to give a solid. The solid obtained was recrystallized from ethanol, whereby 5.9 g of a yellow powdery solid having an 84% yield was obtained as the subject matter.

[Step 2] Synthesis of 9-[4-(carbazol-9-yl)phenyl]-10-(4-trifluoromethylphenyl)fluorene (abbreviation: CF3CzPA)

The synthetic scheme of CF3CzPA is shown in (E-4).

3.0 g (7.5 mmol) of 9-bromo-10-(4-trifluoromethylphenyl)phosphonium, 2.2 g (7.5 mmol) of 4-(carbazol-9-yl)phenylboronic acid and 200 mg (0.66 mmol) of tris(o-tolyl)phosphine was placed in a 100 ml three-necked flask and subjected to nitrogen substitution in the system. 25 ml of toluene and 10 ml (2.0 mol/liter) of potassium carbonate solution were added to the mixture, and the mixture was stirred and degassed under reduced pressure. Then 60 mg (0.27 mmol) of palladium(II) acetate was added. The reaction mixture was at 80 ° C And stirring under a nitrogen stream for 12 hours. The reaction mixture was then washed three times with water. The aqueous layer of the mixture was extracted three times with ethyl acetate, and the extracted solution was washed with brine and brine, and the organic layer was dried over magnesium sulfate. The mixture was naturally filtered to remove magnesium sulfate, and the filtrate was condensed to give a solid, and the solid was purified by silica gel column chromatography (hexane: toluene = 65:35). The obtained solid was recrystallized from hexane, whereby 1.6 g of a pale yellow powdery solid having a yield of 38% was obtained as the subject matter. The compound was confirmed to be 9-[4-(carbazol-9-yl)phenyl]-10-(4-trifluoromethylphenyl)fluorene (abbreviation: CF3CzPA) by nuclear magnetic resonance measurement (NMR).

The ¹ H NMR data of CF3CzPA is shown below. _{^{1 H NMR (300MHz, CDCl 3}} ); δ = 7.33-7.54 (m, 8H), 7.60-7.74 (m, 8H), 7.83-7.92 (m, 6H), 8.22 (d, J = 7.8Hz, 2H) . ^{The 1} H NMR chart is shown in Figures 25A and 25B. It should be noted that the range expansion of 6.5 ppm to 8.5 ppm in Fig. 25A is shown in Fig. 25B.

When 1.5 g of CF3CzPA obtained by the above synthesis method was purified by sublimation for 12 hours under the conditions of an argon gas flow of 20.0 ml/min, a pressure of 200 Torr and a heating temperature of 300 ° C, 56% yield was obtained. The pale yellow needle crystal of 848 mg CF3CzPA.

Thermogravimetric Analysis - Differential Thermal Analysis (TG-DTA) of CF3CzPA was carried out using a thermogravimetric analyzer/differential thermal analyzer (TG/DTA 320, product of Seiko Instruments Inc.). As a result, based on the relationship between gravity and temperature (measured by thermogravimetric analysis), the temperature under normal pressure is 328 ° C, which is the temperature under the gravity of the measurement starting point of gravity of 95% or less. degree. It was found to have favorable heat resistance.

Figure 26 shows the absorption spectrum of a toluene solution of CF3CzPA. Figure 27 shows the absorption spectrum of a film of CF3CzPA. This measurement was carried out using a UV-visible spectrophotometer (V-550, manufactured by JASCO Corporation). The solution was placed in a quartz bath and the film was evaporated on a quartz substrate to form a sample. The absorption spectra from each of the reduced quartz absorption spectra are shown in Figures 26 and 27. In Figs. 26 and 27, the horizontal axis represents the wavelength (nano) and the vertical axis represents the absorption intensity (in units). In the case of the toluene solution, the absorption mainly based on the ruthenium skeleton was found to be about 376 nm and 396 nm, and in the case of the film, the absorption mainly based on the ruthenium skeleton was found at about 380 nm and 402 Nai. Meter. The luminescence spectrum (excitation wavelength: 370 nm) of the toluene solution of CF3CzPA is shown in Fig. 28, and the luminescence spectrum (excitation wavelength: 380 nm) of the film of CF3CzPA is shown in Fig. 29. In Figs. 28 and 29, the horizontal axis represents the wavelength (nano) and the vertical axis represents the luminous intensity (in units). In the example of the toluene solution, the maximum emission wavelength was 428 nm (excitation wavelength: 370 nm), and in the example of the film, it was 444 nm (excitation wavelength: 380 nm).

Further, the HOMO value of CF3CzPA having a film state was -6.01 eV, which was measured in the air by a photoelectron spectrometer (AC-2, manufactured by Riken Keiki Co., Ltd.). Moreover, the absorption limit was obtained from the Tauc plot using data on the absorption spectrum of the CF3CzPA film of Fig. 27. When the absorption limit is evaluated as an optical energy gap, the energy gap is 2.95 eV. Therefore, the HOMO value is -3.06 eV.

Moreover, the oxidation-reduction reaction characteristics of CF3CzPA were measured by cyclic voltammetry (CV) measurement. Further, an electrochemical analyzer (ALS type 600A, manufactured by BAS Inc.) was used for the measurement.

Dehydrated dimethylformamide (DMF, manufactured by Aldrich, 99.8%, catalog number: 22705-6) was used as the solvent for the solution used in the CV measurement. Tetra-n-butylammonium perchlorate (n-Bu ₄ NClO ₄ , manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) is a supporting electrolyte, which is dissolved in a solvent to make perchloric acid The concentration of n-butylammonium is 100 millimoles per liter. Moreover, the object to be measured was dissolved so that its concentration was set to 1 millimol/liter. Further, a platinum electrode (PTE platinum electrode, manufactured by BAS Inc.) was used as the working electrode. A platinum electrode (VC-3 Pt auxiliary electrode (5 cm), manufactured by BAS Inc.) was used as the auxiliary electrode. An Ag/Ag ⁺ electrode (RE5 non-aqueous solvent reference electrode, manufactured by BAS Inc.) was used as a reference electrode. It should be noted that this measurement is carried out at room temperature.

The reduction reaction characteristics of CF3CzPA were measured as follows. After the potential was changed from -0.18 volts to -2.22 volts, the scan of the potential of the working electrode with respect to the reference electrode was changed from -2.32 volts to -0.18 volts, and one cycle was measured, and 100 cycles were measured. Further, the oxidation reaction characteristics of CF3CzPA were measured as follows. After the potential was changed from -0.27 volts to 1.30 volts, the scan with respect to the potential of the working electrode of the reference electrode changed from 1.30 volts to -0.27 volts was set to one cycle, and 100 cycles were measured. Furthermore, the scanning speed of the CV measurement method was set to 0.1 volt/sec.

Figure 62 shows the results of CV measurement at the reducing end of CF3CzPA and Figure 63 shows the results of CV measurement at the oxidation end of CF3CzPA. In Figs. 62 and 63, the horizontal axis shows the potential (volts) of the working electrode with respect to the reference electrode, and the vertical axis shows the current flow value (microamperes) between the working electrode and the auxiliary electrode.

In the CF3CzPA example, the reversible peaks from Figures 62 and 63 are shown at the oxidized and reduced ends. In addition, the peak intensity is not easily changed even when the oxidation is repeated 100 times to reduction or reduction to the oxidation cycle. From the above, it has been found that the anthracene derivative of the present invention is very stable to repeated oxidation-reduction reactions.

[Specific Example 5]

The synthesis method of 9-[4-(carbazol-9-yl)phenyl]-10-(2-naphthyl)anthracene (abbreviation: β NCzPA) represented by the structural formula (16) is described in this specific example. in.

[Step 1] Synthesis of 9-bromo-10-(2-naphthyl)anthracene (i) Synthesis of 9-(2-naphthyl)anthracene

The synthetic scheme of 9-(2-naphthyl)anthracene is shown in (F-1).

Put 5.1 g (20 mmol) of 9-bromoindole, 3.4 g (20 mmol) of 2-naphthylboronic acid and 244 mg (0.80 mmol) of tris(o-tolyl)phosphine into 100 ml three necks In the flask, and carry out nitrogen substitution in the system. 20 ml of ethylene glycol dimethyl ether (DME) was added to the mixture, and the mixture was stirred and degassed under reduced pressure. Then 45 mg (0.20 mmol) of palladium (II) acetate and 10 ml (2.0 mol/L) potassium carbonate solution were added. The reaction mixture was stirred at 80 ° C for 3 hours under a stream of nitrogen. The reaction mixture was then cooled to room temperature, and the precipitated solid was collected by suction filtration. The collected solid was dissolved in toluene, and the solution was subjected to suction filtration through magnesium ruthenate, diatomaceous earth, and then alumina. The filtrate was condensed to give a solid, and the solid was recrystallized from ethanol, whereby 5.6 g of a white powdery solid having a yield of 92% was obtained as the subject matter.

(ii) Synthesis of 9-bromo-10-(2-naphthyl)anthracene

The synthetic scheme of 9-bromo-10-(2-naphthyl)anthracene is shown in (F-2).

5.6 g (18.0 mmol) of 9-(2-naphthyl)anthracene and 90 ml of carbon tetrachloride were placed in a 500 ml three-necked flask and stirred. A solution in which 3.2 g (20 mmol) of bromine was dissolved in 10 ml of carbon tetrachloride was dropped into the above solution through a dropping funnel. The solution was then stirred at room temperature for 1 hour, and an aqueous sodium thiosulfate solution was added to the reaction solution to complete the reaction. The aqueous layer of the reaction mixture was extracted with chloroform, and the extracted solution was washed with a saturated aqueous sodium hydrogen carbonate solution and brine. The organic layer was dried over magnesium sulfate and the mixture was filtered thoroughly to remove magnesium sulfate. The filtrate was then condensed to give a solid. The solid obtained was recrystallized from ethanol, whereby 5.5 g of a yellow powdery solid having a yield of 79% was obtained as the subject matter.

[Step 2] Synthesis of 9-[4-(carbazol-9-yl)phenyl]-10-(2-naphthyl)anthracene (abbreviation: β NCzPA)

The synthetic scheme of β NCzPA is shown in (F-3).

3.0 g (7.8 mmol) of 9-bromo-10-(2-naphthyl)anthracene and 2.3 g (7.8 mmol) of 4-(carbazol-9-yl)phenylboronic acid were placed in 100 ml of three In a neck flask, and carry out nitrogen substitution in the system. 25 ml of ethylene glycol dimethyl ether (DME) and 10 ml (2.0 mol/liter) of potassium carbonate solution were added to the mixture, and the mixture was stirred and degassed under reduced pressure. Then 90 mg (0.017 mmol) of ruthenium (triphenylphosphine) palladium (0) was added. The reaction mixture was stirred at 80 ° C for 12 hours under a stream of nitrogen. The reaction mixture was then washed with water. The aqueous layer of the mixture was extracted with ethyl acetate, and the extracted solution was washed with brine and brine and dried over magnesium sulfate. The mixture was naturally filtered to remove magnesium sulfate. The filtrate was condensed to give a solid, which was purified by silica gel column chromatography (hexane: toluene = 7:3). The obtained solid was recrystallized from hexane, whereby 2.4 g of a pale yellow solid with a yield of 57% was obtained as the subject matter. The compound was confirmed to be 9-[4-(carbazol-9-yl)phenyl]-10-(2-naphthyl)anthracene (abbreviation: β NCzPA) by nuclear magnetic resonance measurement (NMR).

The ¹ H NMR data of β NCzPA is shown below. ¹ H NMR (300 MHz, CDCl ₃ ); δ=7.33-7.56 (m, 9H), 7.59-7.78 (m, 9H), 7.83-7.89 (m, 4H), 7.92-7.95 (m, 1H), 8.01 8.06 (m, 2H), 8.10 (d, J = 8.7 Hz, 1H), 8.22 (d, J = 7.2 Hz, 2H). ^{The 1} H NMR chart is shown in Figures 30A and 30B. It should be noted that the range expansion of 6.5 ppm to 8.5 ppm in Fig. 30A is shown in Fig. 30B.

When 1.79 g of β NCzPA obtained by the above synthesis method was purified by sublimation for 12 hours under the conditions of an argon gas flow of 3.0 ml/min, a pressure of 8.0 Pascal and a heating temperature of 290 ° C, an 89% yield was obtained. 1.59 grams of light yellow needle crystal of β NCzPA.

Thermogravimetric Analysis - Differential Thermal Analysis (TG/DTA) of β NCzPA was carried out using a thermogravimetric analyzer/differential thermal analyzer (TG/DTA 320, product of Seiko Instruments Inc.). As a result, based on the relationship between gravity and temperature (thermogravimetric analysis), the temperature under normal pressure was 368 ° C, which is the temperature under the gravity of the measurement starting point of gravity of 95% or less. It was found to have favorable heat resistance.

Figure 31 shows the absorption spectrum of a toluene solution of β NCzPA. Figure 32 shows the absorption spectrum of a film of β NCzPA. This measurement was carried out using a UV-visible spectrophotometer (V-550, manufactured by JASCO Corporation). The solution was placed in a quartz bath and the film was evaporated on a quartz substrate to form a sample. The absorption spectra from each of the reduced quartz absorption spectra are shown in Figures 31 and 32. In Figs. 31 and 31, the horizontal axis represents the wavelength (nano), and the vertical axis represents the absorption intensity (in units). In toluene In the case of the liquid, the absorption mainly based on the ruthenium skeleton was found to be about 378 nm and 398 nm, and in the case of the film, the absorption mainly based on the ruthenium skeleton was found at about 384 nm and 404 nm. The luminescence spectrum (excitation wavelength: 370 nm) of the toluene solution of β NCzPA is shown in Fig. 33, and the luminescence spectrum (excitation wavelength: 381 nm) of the film of β NCzPA is shown in Fig. 34 . In Figs. 33 and 34, the horizontal axis represents the wavelength (nano) and the vertical axis represents the luminous intensity (in units). In the example of the toluene solution, the maximum emission wavelength was 426 nm (excitation wavelength: 370 nm), and in the example of the film, it was 440 nm (excitation wavelength: 381 nm).

Further, the HOMO value of β NCzPA having a film state was -5.72 eV, which was measured in the air by a photoelectron spectrometer (AC-2, manufactured by Riken Keiki Co., Ltd.). Moreover, the absorption limit was obtained from the Tauc plot using data on the absorption spectrum of the film of β NCzPA in Fig. 32. When the absorption limit is evaluated as an optical energy gap, the energy gap is 2.92 eV. Therefore, the HOMO value is -2.80 eV.

Moreover, the oxidation-reduction reaction characteristics of β NCzPA were measured by cyclic voltammetry (CV) measurement. Further, an electrochemical analyzer (ALS type 600A, manufactured by BAS Inc.) was used for the measurement.

Dehydrated dimethylformamide (DMF, manufactured by Aldrich, 99.8%, catalog number: 22705-6) was used as the solvent for the solution used in the CV measurement. Tetra-n-butylammonium perchlorate (n-Bu ₄ NClO ₄ , manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) is a supporting electrolyte, which is dissolved in a solvent to make perchloric acid The concentration of n-butylammonium is 100 millimoles per liter. Moreover, the object to be measured was dissolved so that its concentration was set to 1 millimol/liter. Further, a platinum electrode (PTE platinum electrode, manufactured by BAS Inc.) was used as the working electrode. A platinum electrode (VC-3 Pt auxiliary electrode (5 cm), manufactured by BAS Inc.) was used as the auxiliary electrode. An Ag/Ag ⁺ electrode (RE5 non-aqueous solvent reference electrode, manufactured by BAS Inc.) was used as a reference electrode. It should be noted that this measurement is carried out at room temperature.

The reduction reaction characteristics of β NCzPA were measured as follows. After the potential was changed from -0.24 volts to -2.40 volts, the scan of the potential of the working electrode with respect to the reference electrode was changed from -2.40 volts to -0.24 volts, and was set to one cycle, and 100 cycles were measured. Further, the oxidation reaction characteristics of β NCzPA were measured as follows. After the potential was changed from -0.30 volts to 1.20 volts, the scan with respect to the potential of the working electrode of the reference electrode changed from 1.20 volts to -0.30 volts was set to one cycle, and 100 cycles were measured. Furthermore, the scanning speed of the CV measurement method was set to 0.1 volt/sec.

Figure 64 shows the results of CV measurement at the reducing end of β NCzPA and Figure 65 shows the results of CV measurement at the oxidation end of β NCzPA. In Figs. 64 and 65, the horizontal axis shows the potential (volts) of the working electrode with respect to the reference electrode, and the vertical axis shows the current flow value (microamperes) between the working electrode and the auxiliary electrode.

In the example of β NCzPA, the reversible peaks from Figures 64 and 65 are shown at the oxidized end and the reduced end. In addition, the peak intensity is not easily changed even when the oxidation is repeated 100 times to reduction or reduction to the oxidation cycle. From the above, it has been found that the anthracene derivative of the present invention is very stable to repeated oxidation-reduction reactions.

[Specific Example 6]

The light-emitting element of the present invention is described in this specific embodiment with reference to FIG. The chemical formula of the materials used in this embodiment is shown below.

The method for producing the light-emitting element of this embodiment is shown below.

First, indium tin oxide (ITSO) containing ruthenium oxide is deposited on the glass substrate 2101 by sputtering to form the first electrode 2102. It should be noted that the thickness is 110 nm and the electrode area is 2 nm x 2 nm.

Next, the substrate on which the first electrode is formed is fixed to the substrate holder provided in the vacuum evaporation apparatus in such a manner that the surface of the substrate has the first electrode facing downward. The voltage is reduced to about 10 ^-4 Å, and then 4,4'-bis[N-(1-naphthyl)-N-anilino]biphenyl (abbreviation: NPB) and molybdenum oxide (VI) are common. Evaporation is performed on the first electrode 2102, thereby forming a layer 2103 containing a composite material of an organic compound and an inorganic compound. The film thickness of the layer 2103 was 50 nm, and the weight ratio between NPB and molybdenum oxide (VI) was set to 4:1 (= NPB: molybdenum oxide). It should be noted that the co-evaporation method is an evaporation method in which an evaporation system is carried out in one processing chamber while being performed by several evaporation sources.

Next, the hole transport layer 2104 having a thickness of 10 nm is used by using a heat-resistant evaporation method using 4,4'-bis[N-(1-naphthyl)-N-anilino]biphenyl (abbreviation: NPB). It is formed on the layer 2103 containing the composite material.

Further, the light-emitting layer 2105 having a thickness of 30 nm is a 9-[4-(N-carbazolyl)]phenyl-10-benzoquinone represented by the structural formula (11) by co-evaporation (abbreviation: CzPA) And N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylindole-4,4'-diamine (abbreviation: YGA2S) formed in a hole On the transport layer 2104. Here, the weight ratio between CzPA and YGA2S was adjusted to 1:0.05 (= CzPA: YGA2S).

Next, an electron transport layer 2106 having a thickness of 10 nm was formed on the light-emitting layer 2105 by using a heat-resistant evaporation method using quinone (5-quinoline) complex aluminum (abbreviation: Alq).

Moreover, an electron injection layer 2107 having a thickness of 20 nm is used by a total of The electron transport layer 2106 is formed by evaporating ginseng (5-quinoline) complex aluminum (abbreviation: Alq) and lithium. Here, the weight ratio between Alq and lithium was adjusted to 1:0.01 (=Alq: lithium).

Next, a second electrode 2108 having a thickness of 200 nm is formed on the electron injection layer 2107 by a heat-resistant evaporation method. Therefore, the light-emitting element 1 is manufactured.

Fig. 35 shows the current density versus luminance characteristics of the light-emitting element 1, Fig. 36 shows its voltage versus luminance characteristics, and Fig. 37 shows its luminance versus current efficiency characteristics. Again, Figure 38 shows the emission spectra obtained at a current of 1 milliamperes. The CIE chromaticity coordinates of the light-emitting element 1 at a luminance of 1064 cd/m 2 are (x = 0.17, y = 0.20) and the luminescence is blue. The current efficiency at a luminance of 1064 cd/m 2 was 4.8 cd/ampere, and at the same time, the voltage was 5.8 volts and the current density was 22.2 mA/cm 2 . In addition, as shown in FIG. 38, the maximum emission wavelength at a current of 1 milliamperes is 444 nm.

[Specific Example 7]

The light-emitting element of the present invention is described in this specific embodiment with reference to FIG. The method for producing the light-emitting element of this embodiment is shown below.

First, indium tin oxide (ITSO) containing ruthenium oxide is deposited on the glass substrate 2101 by sputtering to form the first electrode 2102. It should be noted that the thickness is 110 nm and the electrode area is 2 nm x 2 nm.

Next, the substrate on which the first electrode is formed is fixed to the substrate holder provided in the vacuum evaporation apparatus in such a manner that the surface of the substrate has the first electrode facing downward. The voltage is reduced to about 10 ^-4 Å, and then 4,4'-bis[N-(1-naphthyl)-N-anilino]biphenyl (abbreviation: NPB) and molybdenum oxide (VI) are common. Evaporation is performed on the first electrode 2102, thereby forming a layer 2103 containing a composite material of an organic compound and an inorganic compound. The film thickness of the layer 2103 was 50 nm, and the weight ratio between NPB and molybdenum oxide (VI) was set to 4:1 (= NPB: molybdenum oxide). It should be noted that the co-evaporation method is an evaporation method in which an evaporation system is carried out in one processing chamber while being performed by several evaporation sources.

Next, the hole transport layer 2104 having a thickness of 10 nm is used by using a heat-resistant evaporation method using 4,4'-bis[N-(1-naphthyl)-N-anilino]biphenyl (abbreviation: NPB). It is formed on the layer 2103 containing the composite material.

Further, the light-emitting layer 2105 having a thickness of 30 nm is a 9-(biphenyl-4-yl)-10-[4-(carbazol-9-yl)benzene represented by the structural formula (12) by co-evaporation.蒽] (abbreviation: PPCzPA) and N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylindole-4,4'-diamine (abbreviation :YGA2S) is formed on the hole transport layer 2104. Here, the weight ratio between PPCzPA and YGA2S was adjusted to 1:0.05 (=PPCzPA: YGA2S).

Next, an electron transport layer 2106 having a thickness of 10 nm was formed on the light-emitting layer 2105 by using a heat-resistant evaporation method using quinone (5-quinoline) complex aluminum (abbreviation: Alq).

Moreover, an electron injection layer 2107 having a thickness of 20 nm is used by a total of The electron transport layer 2106 is formed by evaporating ginseng (5-quinoline) complex aluminum (abbreviation: Alq) and lithium. Here, the weight ratio between Alq and lithium was adjusted to 1:0.01 (=Alq: lithium).

Next, a second electrode 2108 having a thickness of 200 nm is formed on the electron injection layer 2107 by a heat-resistant evaporation method. Therefore, the light-emitting element 2 is manufactured.

Fig. 39 shows current density versus luminance characteristics of the light-emitting element 2, Fig. 40 shows its voltage versus luminance characteristics, and Fig. 41 shows its luminance versus current efficiency characteristics. Again, Figure 42 shows the emission spectra obtained at a current of 1 milliamperes. The CIE chromaticity coordinates of the light-emitting element 2 at a luminance of 895 cd/m 2 are (x = 0.17, y = 0.20) and the luminescence is blue. The current efficiency at a luminance of 895 cd/m 2 was 4.4 cd/ampere, and at the same time, the voltage was 5.8 volts and the current density was 20.1 mA/cm 2 . In addition, as shown in FIG. 42, the maximum emission wavelength at a current of 1 milliamperes is 443 nm.

[Embodiment 8]

The light-emitting element of the present invention is described in this specific embodiment with reference to FIG. The method for producing the light-emitting element of this embodiment is shown below.

First, indium tin oxide (ITSO) containing ruthenium oxide is deposited on the glass substrate 2101 by sputtering to form the first electrode 2102. It should be noted that the thickness is 110 nm and the electrode area is 2 nm x 2 nm.

Next, the substrate on which the first electrode is formed is fixed to the substrate holder provided in the vacuum evaporation apparatus in such a manner that the surface of the substrate has the first electrode facing downward. The voltage is reduced to about 10 ^-4 Å, and then 4,4'-bis[N-(1-naphthyl)-N-anilino]biphenyl (abbreviation: NPB) and molybdenum oxide (VI) are common. Evaporation is performed on the first electrode 2102, thereby forming a layer 2103 containing a composite material of an organic compound and an inorganic compound. The film thickness of the layer 2103 was 50 nm, and the weight ratio between NPB and molybdenum oxide (VI) was set to 4:1 (= NPB: molybdenum oxide). It should be noted that the co-evaporation method is an evaporation method in which an evaporation system is carried out in one processing chamber while being performed by several evaporation sources.

Next, the hole transport layer 2104 having a thickness of 10 nm is used by using a heat-resistant evaporation method using 4,4'-bis[N-(1-naphthyl)-N-anilino]biphenyl (abbreviation: NPB). It is formed on the layer 2103 containing the composite material.

Further, the light-emitting layer 2105 having a thickness of 30 nm is a 9-(4-t-butylphenyl)-10-[4-(carbazol-9-yl) represented by the structural formula (20) by co-evaporation. Benzoquinone (abbreviation: PTBCzPA) and N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylindole-4,4'-diamine (abbreviation :YGA2S) is formed on the hole transport layer 2104. Here, the weight ratio between PPCzPA and YGA2S was adjusted to 1:0.05 (=PTBCzPA:YGA2S).

Next, an electron transport layer 2106 having a thickness of 10 nm was formed on the light-emitting layer 2105 by using a heat-resistant evaporation method using quinone (5-quinoline) complex aluminum (abbreviation: Alq).

Moreover, an electron injection layer 2107 having a thickness of 20 nm is used by a total of The electron transport layer 2106 is formed by evaporating ginseng (5-quinoline) complex aluminum (abbreviation: Alq) and lithium. Here, the weight ratio between Alq and lithium was adjusted to 1:0.01 (=Alq: lithium).

Next, a second electrode 2108 having a thickness of 200 nm is formed on the electron injection layer 2107 by a heat-resistant evaporation method. Therefore, the light-emitting element 3 is manufactured.

Fig. 43 shows current density versus luminance characteristics of the light-emitting element 3, Fig. 44 shows its voltage-to-luminance characteristic, and Fig. 45 shows its luminance versus current efficiency characteristics. Again, Figure 46 shows the emission spectra obtained at a current of 1 milliamperes. The CIE chromaticity coordinates of the light-emitting element 3 at a luminance of 1025 cd/m 2 are (x = 0.16, y = 0.16) and the luminescence is blue. The current efficiency at a luminance of 1025 cd/m 2 was 2.2 cd/ampere, and the voltage was 6.2 volts at the same time and the current density was 46.4 mA/cm 2 . In addition, as shown in Fig. 46, the maximum emission wavelength at a current of 1 milliamperes was 442 nm.

[Embodiment 9]

The light-emitting element of the present invention is described in this specific embodiment with reference to FIG. The method for producing the light-emitting element of this embodiment is shown below.

First, indium tin oxide (ITSO) containing ruthenium oxide is deposited on the glass substrate 2101 by sputtering to form the first electrode 2102. It should be noted that the thickness is 110 nm and the electrode area is 2 nm x 2 nm.

Next, the substrate on which the first electrode is formed is fixed to the substrate holder provided in the vacuum evaporation apparatus in such a manner that the surface of the substrate has the first electrode facing downward. The voltage is reduced to about 10 ^-4 Pascals, and then 4,4'-bis[N-(1-naphthyl)-N-anilino]biphenyl (abbreviation: NPB) and molybdenum oxide (VI) are co-evaporated. On the first electrode 2102, a layer 2103 comprising a composite material of an organic compound and an inorganic compound is formed. The film thickness of the layer 2103 was 50 nm, and the weight ratio between NPB and molybdenum oxide (VI) was set to 4:1 (= NPB: molybdenum oxide). It should be noted that the co-evaporation method is an evaporation method in which an evaporation system is carried out in one processing chamber while being performed by several evaporation sources.

Next, the hole transport layer 2104 having a thickness of 10 nm is used by using a heat-resistant evaporation method using 4,4'-bis[N-(1-naphthyl)-N-anilino]biphenyl (abbreviation: NPB). It is formed on the layer 2103 containing the composite material.

Further, the light-emitting layer 2105 having a thickness of 30 nm is a 9-[4-(carbazol-9-yl)phenyl]-10-(2-naphthyl) group represented by the structural formula (16) by co-evaporation.蒽 (abbreviation: β NCzPA) and N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylindole-4,4'-diamine (abbreviation: YGA2S) is formed on the hole transport layer 2104. Here, the weight ratio between β NCzPA and YGA 2S was adjusted to 1:0.05 (=β NCzPA:YGA2S).

Next, an electron transport layer 2106 having a thickness of 10 nm was formed on the light-emitting layer 2105 by using a heat-resistant evaporation method using quinone (5-quinoline) complex aluminum (abbreviation: Alq).

Moreover, an electron injection layer 2107 having a thickness of 20 nm is used by a total of The electron transport layer 2106 is formed by evaporating ginseng (5-quinoline) complex aluminum (abbreviation: Alq) and lithium. Here, the weight ratio between Alq and lithium was adjusted to 1:0.01 (=Alq: lithium).

Next, a second electrode 2108 having a thickness of 200 nm is formed on the electron injection layer 2107 by a heat-resistant evaporation method. Therefore, the light-emitting element 4 is manufactured.

Fig. 47 shows the current density versus luminance characteristics of the light-emitting element 4, Fig. 48 shows its voltage versus luminance characteristics, and Fig. 49 shows its luminance versus current efficiency characteristics. Again, Figure 50 shows the emission spectra obtained at a current of 1 milliamperes. The CIE chromaticity coordinates of the light-emitting element 4 at a luminance of 938 cd/m 2 are (x = 0.18, y = 0.22) and the luminescence is blue. The current efficiency at a luminance of 938 cd/m 2 was 4.3 cd/ampere, and at the same time, the voltage was 6.0 volts and the current density was 21.9 mA/cm 2 . In addition, as shown in FIG. 50, the maximum emission wavelength at a current of 1 milliamperes is 445 nm.

[Specific Example 10]

The light-emitting element of the present invention is described in this specific embodiment with reference to FIG. The method for producing the light-emitting element of this embodiment is shown below.

First, indium tin oxide (ITSO) containing ruthenium oxide is deposited on the glass substrate 2101 by sputtering to form the first electrode 2102. It should be noted that the thickness is 110 nm and the electrode area is 2 nm x 2 nm.

Next, the substrate on which the first electrode is formed is fixed to the substrate holder provided in the vacuum evaporation apparatus in such a manner that the surface of the substrate has the first electrode facing downward. The voltage is reduced to about 10 ^-4 Å, and then 4,4'-bis[N-(1-naphthyl)-N-anilino]biphenyl (abbreviation: NPB) and molybdenum oxide (VI) are common. Evaporation is performed on the first electrode 2102, thereby forming a layer 2103 containing a composite material of an organic compound and an inorganic compound. The film thickness of the layer 2103 was 50 nm, and the weight ratio between NPB and molybdenum oxide (VI) was set to 4:1 (= NPB: molybdenum oxide). It should be noted that the co-evaporation method is an evaporation method in which an evaporation system is carried out in one processing chamber while being performed by several evaporation sources.

Next, the hole transport layer 2104 having a thickness of 10 nm is used by using a heat-resistant evaporation method using 4,4'-bis[N-(1-naphthyl)-N-anilino]biphenyl (abbreviation: NPB). It is formed on the layer 2103 containing the composite material.

Further, the light-emitting layer 2105 having a thickness of 30 nm is a 9-[4-(carbazol-9-yl)phenyl]-10-(4-trifluoromethyl) represented by the structural formula (42) by co-evaporation. Phenyl) hydrazine (abbreviation: CF3CzPA) and N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylindole-4,4'-diamine (abbreviation: YGA2S) is formed on the hole transport layer 2104. Here, the weight ratio between PPCzPA and YGA2S was adjusted to 1:0.05 (=PPCzPA: YGA2S).

Next, an electron transport layer 2106 having a thickness of 10 nm was formed on the light-emitting layer 2105 by using a heat-resistant evaporation method using quinone (5-quinoline) complex aluminum (abbreviation: Alq).

Moreover, an electron injection layer 2107 having a thickness of 20 nm is used by a total of The electron transport layer 2106 is formed by evaporating ginseng (5-quinoline) complex aluminum (abbreviation: Alq) and lithium. Here, the weight ratio between Alq and lithium was adjusted to 1:0.01 (=Alq: lithium).

Next, a second electrode 2108 having a thickness of 200 nm is formed on the electron injection layer 2107 by a heat-resistant evaporation method. Therefore, the light-emitting element 5 is manufactured.

Fig. 51 shows the current density versus luminance characteristics of the light-emitting element 5, Fig. 52 shows its voltage versus luminance characteristics, and Fig. 53 shows its luminance versus current efficiency characteristics. Again, Figure 54 shows the emission spectra obtained at a current of 1 milliamperes. The CIE chromaticity coordinates of the light-emitting element 5 at a luminance of 907 cd/m 2 are (x = 0.20, y = 0.33) and the luminescence is blue. The current efficiency at a luminance of 907 cd/m 2 was 4.5 cd/ampere, and at the same time, the voltage was 6.8 volts and the current density was 20.3 mA/cm 2 . In addition, as shown in Fig. 54, the maximum emission wavelength at a current of 1 milliamperes was 497 nm.

The present application is based on Japanese Patent Application No. 2006-234639, filed on Jan.

101‧‧‧Substrate

102‧‧‧first electrode

103‧‧‧ first floor

104‧‧‧ second floor

105‧‧‧ third floor

106‧‧‧ fourth floor

107‧‧‧Second electrode

Claims (7)

An anthracene derivative represented by the formula (2), Wherein each of R ¹ to R ⁸ in the formula represents hydrogen, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms, wherein Ar ¹ in the formula represents 6 to 25 carbon atoms The aryl group, and X ³ thereof in the formula, represent organotin, trifluoromethanesulfonate, Grignard reagent, organic mercury, thiocyanate, organozinc, organoaluminum, or organozirconium. A method for synthesizing an anthracene derivative represented by the formula (1), which comprises the steps of: coupling an anthracene derivative represented by the formula (2) with a compound represented by the formula (3) by using a metal or a metal compound Carbazole derivatives, Wherein each of R ¹ to R ⁸ in the formula represents hydrogen, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms, wherein Ar ¹ in the formula represents 6 to 25 carbon atoms An aryl group, wherein Ar ² in the formula represents an extended aryl group having 6 to 25 carbon atoms, wherein each of A ¹ and A ² in the formula represents hydrogen, an aryl group having 6 to 25 carbon atoms or has 1 An alkyl group of 4 carbon atoms, wherein X ³ represents an organotin, a trifluoromethanesulfonate, a Grignard reagent, an organic mercury, a thiocyanate, an organozinc, an organoaluminum, or an organozirconium, and X ⁶ in the formula represents an active site. The method of claim 2, wherein the metal or metal compound is used as a catalyst. The method of claim 2, wherein the metal is copper or iron. The method of claim 2, wherein the metal compound is cuprous iodide. The method of claim 3, wherein the catalyst is a palladium catalyst or a nickel catalyst. The method of claim 2, wherein the active site is boric acid or organic boron.